3-iodo-1-phenyl-1-propanol | 62872-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-iodo-1-phenyl-1-propanol
• 英文别名: 3-iodo-1-phenylpropan-1-ol
• CAS: 62872-58-6
• 化学式: C₉H₁₁IO
• 分子量: 262.09
• InChiKey: FGPCEVMDBSCUMO-UHFFFAOYSA-N

物化性质

• 沸点：
  295.4±33.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-iodo-1-phenyl-1-propanol 在 三丁基膦 、 偶氮二甲酸二异丙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 0.25h， 生成 氟西汀
  参考文献：
  名称：

  Preparation of fluoxetine by multiple flow processing steps

  摘要：

  微流技术已成为合成有机化学中一种现代化和时尚的工具，由于其相较于瓶法具有一系列优势，带来了巨大的改进和潜力。本文研究聚焦于流动化学过程在高效多步合成(±)-氟西汀中的应用，作为传统合成方法的替代，并且是利用流动技术完成的少数全合成实例之一。

  DOI：

  10.1039/c0ob00906g
• 作为产物：
  描述：

  环丙基苯 在 碘 作用下， 以 环丁砜 、 氯仿 为溶剂， 生成 3-iodo-1-phenyl-1-propanol
  参考文献：
  名称：

  Cambie,R.C. et al., Journal of the Chemical Society. Perkin transactions I, 1977, p. 226 - 230

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-氯-1-苯基丙醇 、 碘化钠 在 ether-diethyl ether 、 水 、 氯化钠 、 3-iodo-1-phenyl-1-propanol 作用下， 以 丙酮 为溶剂， 反应 84.0h， 以Resulting in 12.5 g of 3-iodo-1-phenyl-1-propanol (compound 15)的产率得到3-iodo-1-phenyl-1-propanol
  参考文献：
  名称：

  Aryloxyphenylpropylamines and their calcium overload blocking

  摘要：

  具有以下式子的新型芳氧基苯基丙胺类化合物：##STR1## 其中X为H、氰基、卤素、卤代烷基、C.sub.1-6-烷氧基、C.sub.1--烷基、C.sub.1-5-酰基、C.sub.3-5-亚烷基、芳氧基或芳基氧基；R为3,4-二甲氧基、芳基或杂环芳基，可选地带有一个或多个氰基、卤代、C.sub.1-6-烷基、C.sub.1-6-烷氧基、C.sub.1-6-烯基、三氟甲基、C.sub.3-5-亚烷基、芳氧基或芳基氧基；R.sup.1和R.sup.2分别为C.sub.1-10-烷基、C.sub.3-7-环烷基、C.sub.2-10-烯基、C.sub.3-6-环烷基-C.sub.1-5-烷基，可选地带有C.sub.1-5-烷氧基或氰基；或者R.sup.1和R.sup.2可以一起形成一个碳环，以及其与药学上可接受的酸盐，但R.sup.1不是C.sub.3-7-环烷基、C.sub.1-10-烷基或烯基，可以是直链、支链或环状、未取代或带有C.sub.1-4-烷氧基、芳氧基或环烷基或环烷基烷基，在X为H且R.sup.2为甲基基团时。这些新型化合物可用于缺氧、偏头痛、缺血、癫痫、创伤性损伤和神经退行性疾病的治疗。

  公开号：

  US05310756A1

文献信息

• Reactions of silver(<scp>I</scp>) acetate–iodine and thallium(<scp>I</scp>) acetate–iodine with substituted cyclopropanes
  作者：Peter H. Atkinson、Richard C. Cambie、Graham Dixon、Wendy I. Noall、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1039/p19770000230

  日期：——

  Treatment of phenylcyclopropane with silver(I) acetate–iodine or thallium(I) acetate–iodine gives, as the major products, 1,3-disubstituted phenylpropanes resulting from cyclopropane ring opening, and in some cases, from solvolysis of intermediate iodo-acetates. Similar products are given with silver(I) trifluoroacetate–iodine but in this case aromatic iodination also occurs. Treatment of norcarane

  用乙酸碘化银（I）或乙酸碘化th（I）处理苯基环丙烷，作为主要产物，是由环丙烷开环以及某些情况下由中间碘代乙酸盐的溶剂化产生的1,3-二取代苯基丙烷。三氟乙酸银（I）-碘也可提供类似的产品，但在这种情况下也会发生芳族碘化。用相同的试剂处理正二十烷也会导致开环，但此处的副产物是通过消除和随后添加而产生的。两种底物对烯烃对每种试剂的反应性均不如烯烃。讨论了反应机理。据报道其他涉及亲电碘与苯基环丙烷和正戊烷的试剂系统的作用。
• Simplified Heterocyclic Analogues of Fluoxetine Inhibit Inducible Nitric Oxide Production in Lipopolysaccharide-Induced BV2 Cells
  作者：Ju-Young Park、Seung-Woo Kim、Ja-Kyeong Lee、Weon Bin Im、Byung Kwan Jin、Sung-Hwa Yoon

  DOI：10.1248/bpb.34.538

  日期：——

  A series of fluoxetine, where the N-methylamino group was replaced and then simplified, were synthesized and their inhibitory effect was tested for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in lipopolysaccharide (LPS)-induced BV2 cells. Although the synthesized compounds generally revealed weaker activity or greater cytotoxicity than fluoxetine, compound 10a, in which the N-methylamino group in fluoxetine was replaced by morpholine, and the trifluoromethylphenyl ring was substituted with simple oxo group, suppressed NO production dose-dependently at 10, 20 and 40 μM concentrations with less cytotoxicity than fluoxetine, and inhibited iNOS mRNA and protein expression at the same concentrations in LPS-induced BV2 cells. The results suggested that the trifluoromethylphenyl ring moiety in fluoxetine is not necessary for the suppression of NO production and that 10a has the potential as a potent inhibitor of NO production.

  合成了一系列氟西汀，替换并简化了N-甲基氨基团，并测试了它们对脂多糖（LPS）诱导的BV2细胞中一氧化氮（NO）产生和诱导性NO合酶（iNOS）表达的抑制作用。尽管合成的化合物一般显示出比氟西汀弱的活性或更大的细胞毒性，但化合物10a中氟西汀的N-甲基氨基团被莫尔夫啉替换，且三氟甲基苯环被简单的氧基取代，在10、20和40μM浓度下以剂量依赖的方式抑制了NO的产生，且其细胞毒性低于氟西汀，在同样浓度下抑制了LPS诱导的BV2细胞中的iNOS mRNA和蛋白表达。结果表明，氟西汀中的三氟甲基苯环结构对于抑制NO产生并不是必需的，且10a具备作为NO产生强效抑制剂的潜力。
• Aryloxyphenylpropylamines their preparation and use
  申请人：Novo Nordisk A/S

  公开号：US05145870A1

  公开（公告）日：1992-09-08

  Novel aryloxyphenylpropylamines having the formula ##STR1## wherein X is H, cyano, halogen, halogenoalkyl, C.sub.1-6 -alkoxy, C.sub.1-6 -alkyl, C.sub.1-5 -alkanoyl, C.sub.3-5 -alkylene, aryloxy or aralkoxy, and R is 3,4-methylenedioxy, aryl or heteroaryl which are optionally substituted with one or more cyano, halogeno, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, C.sub.1-6 -alkenyl, trifluoromethyl, C.sub.3-5 -alkylene, aryloxy or aralkoxy; and R.sup.1 and R.sup.2 independently is C.sub.1-10 -alkyl, C.sub.3-7 -cycloalkyl, C.sub.2-10 -alkenyl, C.sub.3-6 -cycloalkyl-C.sub.1-5 -alkyl, optionally substituted with C.sub.1-5 -alkoxy or cyano; R.sup.1 and R.sup.2 may together form a carbocyclic ring and a salt thereof with a pharmaceutically acceptable acid, provided however that R.sup.1 is not C.sub.3-7 -cycloalkyl, C.sub.1-10 -alkyl, or alkenyl which may be straight, branched or cyclic, unsubstituted or substituted with C.sub.1-4 -alkoxy, aryloxy or cycloalkyl or cycloalkylalkyl, when X is H and R.sup.2 is a methyl group. The novel compounds are useful in the treatment of anoxia, migraine, ischemia, epilepsy, traumatic injury and neurodegenerative diseases.

  具有以下结构式的新型芳基氧基苯基丙胺类化合物，其中X为H、氰基、卤素、卤代烷基、C.sub.1-6-烷氧基、C.sub.1-6-烷基、C.sub.1-5-烷酰基、C.sub.3-5-烷基烯、芳基氧基或芳基烷氧基，R为3,4-亚甲二氧基、芳基或杂环芳基，可选地取代一个或多个氰基、卤代基、C.sub.1-6-烷基、C.sub.1-6-烷氧基、C.sub.1-6-烯基、三氟甲基、C.sub.3-5-烷基烯、芳基氧基或芳基烷氧基；R.sup.1和R.sup.2独立地为C.sub.1-10-烷基、C.sub.3-7-环烷基、C.sub.2-10-烯基、C.sub.3-6-环烷基-C.sub.1-5-烷基，可选地取代为C.sub.1-5-烷氧基或氰基；R.sup.1和R.sup.2可共同形成一个碳环，并与药用可接受的酸形成盐，但R.sup.1不为C.sub.3-7-环烷基、C.sub.1-10-烷基或烯基，可为直链、支链或环状，未取代或取代为C.sub.1-4-烷氧基、芳基氧基或环烷基或环烷基烷基，当X为H且R.sup.2为甲基基团时。这些新型化合物可用于治疗缺氧、偏头痛、缺血、癫痫、创伤性损伤和神经退行性疾病。
• SHi Reactions at Silicon as Unimolecular Chain Transfer Steps in the Formation of Cyclic Alkoxysilanes
  作者：Armido Studer

  DOI：10.1002/(sici)1521-3773(19980302)37:4<462::aid-anie462>3.0.co;2-m

  日期：1998.3.2

  A new radical approach to cyclic ethers 2 is offered by the intramolecular homolytic substitution (SH i) reaction at a silicon center. High diastereoselectivities can be obtained in this efficient unimolecular chain transfer reaction. Less suitable are radicals such as 1 in which an R3 Si group replaces the SnMe3 group.

  通过在硅中心的分子内均质取代（S H i）反应，提供了一种新的自由基醚基自由基方法。在这种有效的单分子链转移反应中可以获得高的非对映选择性。不太合适的是自由基，例如1，其中R 3 Si基团取代了SnMe 3基团。
• Propanolamine derivatives, their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0576766A1

  公开（公告）日：1994-01-05

  Compounds of formula I wherein X is phenyl unsubstituted or optionally substituted with one or more cyano, halogeno, halogenoalkyl, C1-6-alkoxy, C1-6-alkyl, C1-5-alkanoyl, C3-5-alkenyl, aryloxy, aralkoxy, amino, C1-6-alkyl mono or disubstituted amino, C1-4-alkanoylamino, carbamoyl, C1-4-alkyl N-mono or disubstituted carbamoyl, C1-4-alkyl substituted with amino, C1-2-alkyl mono or disubstituted amino, N0₂, morpholino or imidazolyl; and R is 3,4-methylenedioxyphenyl, aryl or heteroaryl all of which can be optionally substituted with one or more cyano, halogeno, C1-6-alkyl, C1-6-alkoxy, C2-6-alkenyl, trifluoromethyl, C3-5-alkylene, aryloxy, aralkoxy or C1-6-alkylthio; and R¹ and R² are C1-10-alkyl, C3-7-cycloalkyl, C2-10-alkenyl, C3-6-cycloalkyl-C1-5-alkyl, all of which can be unsubstituted or substituted with C1-5-alkyl, C1-5-alkoxy or cyano; or R¹ and R² together form a 5, 6 or 7 membered ring containing at least one nitrogen atom, or which optionally contains two nitrogen atoms, one or two oxygen atom(s) or one or two sulphur atom(s) or a combination thereof, which ring is unsubstituted or optionally substituted with C1-4-alkyl, C1-4-alkoxy or aryl; and R³, R⁴, R⁵, R⁶, and R⁷ independently are hydrogen, C1-4-alkyl or phenyl; or R⁴ and X together form a carbocyclic ring containing 5 or 6 atoms, or a salt thereof with a pharmaceutically acceptable acid; provided however that R¹ and R² are not C3-7-cycloalkyl, C1-10-alkyl or C2-10-alkenyl which may be straight, branched or cyclic, unsubstituted or substituted with C1-4-alkoxy, aryloxy or cycloalkyl, cyano or cycloalkylalkyl, when X is phenyl substituted with cyano, halogen, halogenalkyl, C1-6-alkoxy, C1-6-alkyl, C1-5-alkanoyl, C3-5-alkylene, aryloxy or aralkoxy, are useful in the treatment of anoxia, traumatic injury, ischemia, migraine, epilepsy, Parkinson's disease, Alzheimer's disease and other neurodegenerative diseases.

  化合物的公式I，其中X是苯基，未取代或可选地取代一个或多个氰基，卤基，卤代烷基，C1-6-烷氧基，C1-6-烷基，C1-5-酰基，C3-5-烯基，芳氧基，芳基氧基，氨基，C1-6-烷基单取代或双取代氨基，C1-4-酰胺基，氨基甲酰基，C1-4-烷基N-单取代或双取代的氨基甲酰基，C1-4-烷基取代氨基，C1-2-烷基单取代或双取代氨基，N0₂，吗啉基或咪唑基；以及R是3,4-亚甲二氧基苯基，芳基或杂环芳基，所有这些都可以可选地取代一个或多个氰基，卤基，C1-6-烷基，C1-6-烷氧基，C2-6-烯基，三氟甲基，C3-5-亚烷基，芳基氧基，芳基氧基或C1-6-烷硫基；以及R¹和R²是C1-10-烷基，C3-7-环烷基，C2-10-烯基，C3-6-环烷基-C1-5-烷基，所有这些都可以未取代或取代C1-5-烷基，C1-5-烷氧基或氰基；或R¹和R²一起形成一个含有至少一个氮原子的5、6或7元环，或可选地含有两个氮原子，一个或两个氧原子或一个或两个硫原子或其组合，该环未取代或可选地取代C1-4-烷基，C1-4-烷氧基或芳基；以及R³、R⁴、R⁵、R⁶和R⁷分别是氢，C1-4-烷基或苯基；或者R⁴和X一起形成一个含有5或6个原子的碳环，或其与药学上可接受的酸的盐；但是，当X是取代有氰基，卤基，卤代烷基，C1-6-烷氧基，C1-6-烷基，C1-5-酰基，C3-5-亚烷基，芳氧基或芳基氧基时，R¹和R²不是C3-7-环烷基，C1-10-烷基或C2-10-烯基，可以是直链，支链或环状，未取代或取代有C1-4-烷氧基，芳氧基或环烷基，氰基或环烷基烷基。这些化合物在缺氧，创伤性损伤，缺血，偏头痛，癫痫，帕金森病，阿尔茨海默病和其他神经退行性疾病的治疗中是有用的。