3-methylthio-3-phenyl-1-propanol

• 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-methylthio-3-phenyl-1-propanol
• 英文别名: 3-Methylsulfanyl-3-phenylpropan-1-ol；3-methylsulfanyl-3-phenylpropan-1-ol
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: XYDYDSODXGVJLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylthio-3-phenyl-1-propanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以55%的产率得到(3-bromo-1-phenylpropyl)(methyl)sulfane
  参考文献：
  名称：

  通过路易斯酸活化（γ-甲氧基）烷基金（I）配合物形成环丙烷

  摘要：

  在−78°C下用AlCl 3处理3-甲氧基-3-苯基丙基金（P）AuCH 2 CH 2 CH（OMe）Ph [ P = P（t -Bu）2 o-联苯]金导致立即（≤5分钟）形成苯基环丙烷和（1-甲氧基丙基）苯的4：1混合物，合并产率为86±5％。立体化学纯的异构体赤型-（P）AuCH 2 CHDCH（OMe）Ph的路易斯酸活化导致顺式形成-2-氘代-1-苯基环丙烷为单一立体异构体，产率为84±5％，这表明环丙烷化是随着γ-立体中心的反转而发生的。同样，立体化学纯的环己基金配合物顺式-（P）Au CHCH 2 CH（OMe）CH 2 CH 2 CH 2在-78°C下电离形成双环[3.1.0]己烷，产率为82％±5％，验证了涉及α-立体中心反转的环丙烷化低能途径。综上所述，这些观察结果与环丙烷形成机理一致，该机理涉及Cγ离去基团和Cα（L）Au +片段通过W形过渡态向后位移。

  DOI：

  10.1021/acs.organomet.0c00324
• 作为产物：
  描述：

  环氧乙烷 、 苄基甲基硫醚 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 为溶剂， 以76%的产率得到3-methylthio-3-phenyl-1-propanol
  参考文献：
  名称：

  A palladium complex with a new hemilabile amino- and sulfur-containing phosphinite ligand as an efficient catalyst for the Heck reaction of aryl bromides with styrene. The effect of the amino group

  摘要：

  A palladium complex with a new hemilabile amino- and sulfur-containing phosphinite ligand has been synthesised and its crystal structure determined. This system efficiently catalyses the Heck reaction of aryl bromides with styrene at 130degreesC after 24 h, with turnover numbers of up to 100000 and with a selectivity towards trans-stilbenes ranging from 91.5 to 96.3%. The analogous sulfur-containing phosphinite without the amino group has also been synthesised and subjected to the Heck reaction. The constructive role of the amino group on the formation of the P,S-chelate palladium complex as well as in the Heck reaction is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00474-5

文献信息

• Asymmetric Tandem Michael-Aldol Reactions between 3-Cinnamoyloxazolidine-2-thiones and Aldehydes
  作者：Hironori Kinoshita、Takashi Osamura、Kazumi Mizuno、Sayaka Kinoshita、Tatsunori Iwamura、Shin-ichi Watanabe、Tadashi Kataoka、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1002/chem.200501435

  日期：2006.5.3

  Reactions between chiral 3-cinnamoyl-4-methyl-5-phenyl-1,3-oxazolidine-2-thiones and aromatic aldehydes in the presence of BF3Et2O diastereoselectively produced tricyclic compounds incorporating a bridgehead carbon bound to four heteroatoms in high yields. Four stereocenters were induced during the reaction. The tricyclic products were transformed into propane-1,3-diols bearing three consecutive stereocenters

  在BF 3 Et 2 O非对映选择性地存在下，手性3-肉桂酰基-4-甲基-5-苯基-1，3-恶唑烷-2-硫酮与芳族醛之间的反应以高收率选择性地结合了桥键碳与四个杂原子结合的三环化合物。在反应过程中诱导了四个立体中心。通过酸水解，S-甲基化和手性助剂的还原去除，将三环产物转化为带有三个连续立体中心的丙烷-1,3-二醇。
• Formation of Cyclopropanes via Activation of (γ-Methoxy)alkyl Gold(I) Complexes with Lewis Acids
  作者：Nana Kim、Ross A. Widenhoefer

  DOI：10.1021/acs.organomet.0c00324

  日期：2020.9.14

  Treatment of the gold 3-methoxy-3-phenylpropyl complex (P)AuCH2CH2CH(OMe)Ph [P = P(t-Bu)2o-biphenyl] with AlCl3 at −78 °C led to the immediate (≤5 min) formation of a 4:1 mixture of phenylcyclopropane and (1-methoxypropyl)benzene in 86 ± 5% combined yield. Lewis acid activation of the stereochemically pure isotopomer erythro-(P)AuCH2CHDCH(OMe)Ph led to the formation of cis-2-deuterio-1-phenylcyclopropane

  在−78°C下用AlCl 3处理3-甲氧基-3-苯基丙基金（P）AuCH 2 CH 2 CH（OMe）Ph [ P = P（t -Bu）2 o-联苯]金导致立即（≤5分钟）形成苯基环丙烷和（1-甲氧基丙基）苯的4：1混合物，合并产率为86±5％。立体化学纯的异构体赤型-（P）AuCH 2 CHDCH（OMe）Ph的路易斯酸活化导致顺式形成-2-氘代-1-苯基环丙烷为单一立体异构体，产率为84±5％，这表明环丙烷化是随着γ-立体中心的反转而发生的。同样，立体化学纯的环己基金配合物顺式-（P）Au CHCH 2 CH（OMe）CH 2 CH 2 CH 2在-78°C下电离形成双环[3.1.0]己烷，产率为82％±5％，验证了涉及α-立体中心反转的环丙烷化低能途径。综上所述，这些观察结果与环丙烷形成机理一致，该机理涉及Cγ离去基团和Cα（L）Au +片段通过W形过渡态向后位移。
• A palladium complex with a new hemilabile amino- and sulfur-containing phosphinite ligand as an efficient catalyst for the Heck reaction of aryl bromides with styrene. The effect of the amino group
  作者：Ioannis D Kostas、Barry R Steele、Aris Terzis、Svetlana V Amosova

  DOI：10.1016/s0040-4020(03)00474-5

  日期：2003.5

  A palladium complex with a new hemilabile amino- and sulfur-containing phosphinite ligand has been synthesised and its crystal structure determined. This system efficiently catalyses the Heck reaction of aryl bromides with styrene at 130degreesC after 24 h, with turnover numbers of up to 100000 and with a selectivity towards trans-stilbenes ranging from 91.5 to 96.3%. The analogous sulfur-containing phosphinite without the amino group has also been synthesised and subjected to the Heck reaction. The constructive role of the amino group on the formation of the P,S-chelate palladium complex as well as in the Heck reaction is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.