(E)-10-碘-9-十一碳烯-1-醇 | 132260-47-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: (E)-10-碘-9-十一碳烯-1-醇
• 英文名称: (E)-10-iodo-9-undecen-1-ol
• 英文别名: (E)-10-iododec-9-en-1-ol；(9E)-10-iododecen-1-ol
• CAS: 132260-47-0
• 化学式: C₁₀H₁₉IO
• 分子量: 282.165
• InChiKey: SKAMWMQALNIMRC-VQHVLOKHSA-N

物化性质

• 沸点：
  314.0±15.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (E)-10-碘-9-十一碳烯-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 2-甲基-2-丁烯 、 dimethyl sulfide borane 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 (E10,Z12)-hexadeca-10,12-dien-1-ol
  参考文献：
  名称：

  Pd催化末端炔烃的氢化锡锡合成E-乙烯基碘

  摘要：

  E-乙烯基碘化物可通过一锅反应制备，该反应包括钯催化末端炔烃的氢化锡锡烷化反应，然后对中间乙烯基锡烷进行碘解。该合成耐受官能团，例如醇和酯。

  DOI：

  10.1016/j.tet.2011.10.104
• 作为产物：
  描述：

  8-溴辛酸 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 Schwartz's reagent 、 硼烷四氢呋喃络合物 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 94.17h， 生成 (E)-10-碘-9-十一碳烯-1-醇
  参考文献：
  名称：

  Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone

  摘要：

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).

  DOI：

  10.1021/jo00008a053

文献信息

• Sex attractant pheromone of the pecan nut casebearer (Lepidoptera: Pyralidae)
  作者：Jocelyn G. Millar、Allen E. Knudson、J.Steven McElfresh、Regine Gries、Gerhard Gries、James H. Davis

  DOI：10.1016/0968-0896(96)00010-7

  日期：1996.3

  A female-produced sex pheromone for the pecan nut casebearer, Acrobasis nuxvorella Neunzig, has been identified from pheromone gland extracts of calling female moths. The compound (9E,11Z)-hexadecadienal [(9E,11Z)-16:Ald] was identified by coupled GC-EAD and retention time matches with a synthetic standard on four capillary GC columns of different polarities. Corroboration of the identification of (9E, 11Z)-16:Ald by other analytical chemistry methods was not possible due to the minute quantities of pheromone extracted (<1 picogram/female). In field studies, gray rubber septa impregnated with 100 mu g of synthetic (9E,11Z)-16:Ald were attractive to male moths, whereas higher and lower doses were less attractive. The homologous (9E,11Z)-15:Ald was also slightly attractive, while the more highly conjugated analogues, (9E,11Z,13Z)- and (9E, 11Z,13E)-16:Ald, were not. Copyright (C) 1996 Elsevier Science Ltd
• Makabe, Hidefumi; Tanaka, Akira; Oritani, Takayuki, Journal of the Chemical Society. Perkin transactions I, 1994, # 14, p. 1975 - 1982
  作者：Makabe, Hidefumi、Tanaka, Akira、Oritani, Takayuki

  DOI：——

  日期：——
• (9Z)-9,13-Tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer
  作者：Jocelyn G. Millar、Mark Hoddle、J. Stephen McElfresh、Yunfan Zou、Christina Hoddle

  DOI：10.1016/j.tetlet.2008.06.019

  日期：2008.8

  The highly unsaturated aldehyde (9Z)-9,13-tetradecadien-11-ynal and the corresponding alcohol were identified as possible sex pheromone components of the avocado seed moth, Stenoma catenifer. The aldehyde as a single component attracted more male moths than caged virgin female moths, and addition of the analogous alcohol and/or acetate decreased attraction. A stereospecific synthesis of the pheromone is described. (C) 2008 Elsevier Ltd. All rights reserved.
• KALIVRETENOS, A.;STILLE, J. K.;HEGEDUS, L. S., J. ORG. CHEM., 56,(1991) N, C. 2883-2894
  作者：KALIVRETENOS, A.、STILLE, J. K.、HEGEDUS, L. S.

  DOI：——

  日期：——
• Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone
  作者：A. Kalivretenos、J. K. Stille、L. S. Hegedus

  DOI：10.1021/jo00008a053

  日期：1991.4

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).