(E)-2-(iodomethylene)cyclohexanone | 68655-16-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-2-(iodomethylene)cyclohexanone
• 英文别名: (E)-2-iodomethylenecyclohexanone；2-(Iodmethyliden)-cyclohexanon；(2E)-2-(iodomethylidene)cyclohexan-1-one
• CAS: 68655-16-3
• 化学式: C₇H₉IO
• 分子量: 236.052
• InChiKey: NJQHDRGYCBWCQC-AATRIKPKSA-N

物化性质

• 熔点：
  15 °C
• 沸点：
  60-70 °C(Press: 0.4 Torr)
• 密度：
  1.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-(iodomethylene)cyclohexanone 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 为溶剂， 反应 2.75h， 生成 (E)-((6-(cyclopropylmethylene)cyclohex-1-en-1-yl)oxy)trimethylsilane
  参考文献：
  名称：

  Piers, Edward; Lau, Cheuk Kun; Nagakura, Isao, Canadian Journal of Chemistry, 1983, vol. 61, p. 288 - 297

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯磺酰氯 在 吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (E)-2-(iodomethylene)cyclohexanone
  参考文献：
  名称：

  5,6-Benzo analogues or prostaglandin E

  摘要：

  本文披露了具有下列结构式的前列腺素类似物：其中：T选自羧基、烷氧羰基或氰基组成的群；M选自羰基、R-羟甲亚甲基或S-羟甲亚甲基组成的群；L选自亚甲基或亚甲烷基组成的群，只有在J为亚甲基时L才为亚甲烷基；J选自亚甲基、乙烯基、R-羟甲亚甲基、S-羟甲亚甲基或亚甲基组成的群，只有在L为亚甲烷基时J才为亚甲基；W选自--CH.sub.2 --CH--或trans --CH.dbd.C--组成的群；T.sub.1和T.sub.2连接到相邻的碳原子上；T.sub.1选自氢或苯基，只有当T.sub.2为较低的烷基时T.sub.1才为苯基；T.sub.2选自正戊基或较低的烷基，只有当T.sub.1为苯基时T.sub.2才为较低的烷基；或者T.sub.1和T.sub.2连接在一起形成含有4个或6个碳原子的烷基基团。还公开了制备这种前列腺素类似物的方法。

  公开号：

  US04096336A1

文献信息

• 5,6-Benzo analogues of prostaglandin E
  申请人：Miles Laboratories, Inc.

  公开号：US04097516A1

  公开（公告）日：1978-06-27

  Disclosed are prostaglandin analogues having the structural formula, ##STR1## in which: T is selected from the group consisting of carboxyl, alkoxycarbonyl or cyano; M is selected from the group consisting of carbonyl, R-hydroxymethylene or S-hydroxymethylene; L is selected from the group consisting of methylene or methine, provided L is methine only if J is methine; J is selected from the group consisting of methylene, ethylene, R-hydroxymethylene, S-hydroxymethylene or methine, provided J is methine only if L is methine; W is selected from the group consisting of --CH.sub.2 --CH-- or trans --CH.dbd.C--; T.sub.1 and T.sub.2 are attached to adjacent carbon atoms; T.sub.1 is selected from the group consisting of hydrogen or phenyl, provided T.sub.1 is phenyl only if T.sub.2 is lower alkyl; T.sub.2 is selected from the group consisting of n-pentyl or lower alkyl, provided T.sub.2 is lower alkyl only if T.sub.1 is phenyl; Or T.sub.1 and T.sub.2 are joined together to form an alkylene group of 4 or 6 carbon atoms. Also disclosed are methods for preparing such prostaglandin analogues.

  揭示了具有结构式##STR1##的前列腺素类似物，其中：T从羧基，烷氧羰基或氰基组成的群体中选择；M从羰基，R-羟甲基或S-羟甲基组成的群体中选择；L从亚甲基或甲烷基组成的群体中选择，前提是只有当J为亚甲基时，L才是亚甲基；J从亚甲基，乙烯基，R-羟甲基，S-羟甲基或甲烷基组成的群体中选择，前提是只有当L为亚甲基时，J才是亚甲基；W从--CH.sub.2 --CH--或trans --CH.dbd.C--组成的群体中选择；T.sub.1和T.sub.2连接到相邻的碳原子上；T.sub.1从氢或苯基组成的群体中选择，前提是只有当T.sub.2为较低烷基时，T.sub.1才是苯基；T.sub.2从n-戊基或较低烷基组成的群体中选择，前提是只有当T.sub.1为苯基时，T.sub.2才是较低烷基；或者T.sub.1和T.sub.2结合在一起形成4或6个碳原子的烷基基团。还公开了制备这种前列腺素类似物的方法。
• Synthesis of β-chloro, β-bromo, and β-iodo α,β-unsaturated ketones
  作者：Edward Piers、John R. Grierson、Cheuk Kun Lau、Isao Nagakura

  DOI：10.1139/v82-033

  日期：1982.1.15

  A new, efficient method for the preparation of β-chloro, β-bromo, and β-iodo α,β-unsaturated ketones is described. The method involves the reaction of β-diketones or α-hydroxymethylenecycloalkanones with triphenylphosphine dihalides in the presence of triethylamine. With the dichloride and dibromide reagents, the reactions are conveniently carried out in benzene at room temperature, while with triphenylphosphine diiodide the reactions are best performed in refluxing acetonitrile (β-diketones) or in acetonitrile–hexamethylphosphoramide (α-hydroxymethylenecycloalkanones). The reaction of triphenylphosphine diiodide – triethylamine with a series of 4-alkyl-1,3-cyclohexanediones provides mainly or exclusively (depending on the size of the alkyl group) 6-alkyl-3-iodo-2-cyclohexen-1-ones, while reaction of this reagent with 2-hydroxymethylenecyclohexanone and 2-hydroxymethylenecyclopentanone affords stereoselectively and regioselectively (E)-2-iodomethylenecyclohexanone and (E)-2-iodomethylenecyclopentanone, respectively.

  描述了一种制备β-氯、β-溴和β-碘α，β-不饱和酮的新的高效方法。该方法涉及β-二酮或α-羟甲基环戊酮与三苯基膦二卤化物在三乙胺存在下的反应。对于二氯化物和二溴化物试剂，反应通常在苯中室温下进行，而对于三苯基膦二碘化物，最好在回流的乙腈（β-二酮）或乙腈-六甲基磷酰胺（α-羟甲基环戊酮）中进行。三苯基膦二碘化物-三乙胺与一系列4-烷基-1,3-环己二酮的反应主要或仅产生（取决于烷基的大小）6-烷基-3-碘-2-环己烯-1-酮，而该试剂与2-羟甲基环己酮和2-羟甲基环戊酮的反应分别选择性地产生（E）-2-碘甲基环己酮和（E）-2-碘甲基环戊酮。
• 1,3-Dipolar Cycloaddition of Diazomethane to 1,1-Difluoroallylphosphonates: Application to Synthesis of Cyclopropane Derivatives Having a Diethoxyphosphoryldifluoromethylene Unit
  作者：Tsutomu Yokomatsu、Kenji Suemune、Tetsuo Murano、Shiroshi Shibuya

  DOI：10.3987/com-01-s(k)35

  日期：——

  1,3-Dipolar cycloaddition of diazomethane to (1,1-difluoroallyl)phosphonates was examined to give pyrazolines functionalized by a diethoxyphosphoryldifluoromethylene unit. The pyrazolines were transformed to the cyclopropane derivatives possessing a diethoxyphosphoryldifluoromethylene functionality by photolysis.

  研究了重氮甲烷与 (1,1-二氟烯丙基) 膦酸酯的 1,3-偶极环加成反应，得到了由二乙氧基磷酰基二氟亚甲基单元官能化的吡唑啉。吡唑啉通过光解转化为具有二乙氧基磷酰二氟亚甲基官能团的环丙烷衍生物。
• A Gold-Catalyzed Unique Cycloisomerization of 1,5-Enynes:  Efficient Formation of 1-Carboxycyclohexa-1,4-dienes and Carboxyarenes
  作者：Shaozhong Wang、Liming Zhang

  DOI：10.1021/ja066220f

  日期：2006.11.1

  A novel Au-catalyzed migratory cycloisomerization strategy is advanced. Implementation of this strategy led to the development of a unique Au-catalyzed 1,5-enyne cycloisomerizatioin involving carboxy migration and Au-mediated C-C single bond formation. 1-Carboxycyclohexa-1,4-dienes and carboxyarenes can be prepared with good efficiency and with flexible substitution patterns.
• Piers, Edward; Morton, Howard E.; Nagakura, Isao, Canadian Journal of Chemistry, 1983, vol. 61, p. 1226 - 1238
  作者：Piers, Edward、Morton, Howard E.、Nagakura, Isao、Thies, Richard W.

  DOI：——

  日期：——