2-((E)-hex-1-enyl)cyclohex-1-enecarbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 2-((E)-hex-1-enyl)cyclohex-1-enecarbaldehyde
• 英文别名: 2-hex-1-enylcyclohex-1-ene-1-carbaldehyde；2-[(E)-hex-1-enyl]cyclohexene-1-carbaldehyde
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: ZALWNJSPEBHASN-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2-((E)-hex-1-enyl)cyclohex-1-enecarbaldehyde 在 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以92%的产率得到2-butyl-2,4,5,6,7,7a-hexahydro-inden-1-one
  参考文献：
  名称：

  Metal-Catalyzed Chemoselective Cycloisomerization of cis-2,4-Dien-1-als to 3-Cyclopentenones and 4-Alkylidene-3,4-dihydro-2H-pyrans

  摘要：

  [GRAPHICS]PtCl2 (5 mol %) catalyst effected cycloisomerization of cis-2,4-dien-1-al (1) to 3-cyclopentenone (3) efficiently in hot toluene. In the presence of p-TSA, this PtCl2 catalysis gave 2-cyclopentenone (5) exclusively because of the secondary isomerization reaction. Although the 1-2 equilibrium state greatly favors aldehyde (1), PdCl2(PhCN)(2)(5 mol %) catalyzed cycloisomerization of aldehyde (1) to 4,6,7,8-tetrahydro-3H-isochromene (4) smoothly in hot toluene. A plausible mechanism is proposed on the basis of reaction observation and isotope-labeled experiment.

  DOI：

  10.1021/ol061248h

文献信息

• Gold-Catalyzed Deoxygenated Cyclization of <i>cis</i>-2,4-Dien-1-als with Regioselective Addition of Two Nucleophiles. One-Pot Synthesis of Highly Functionalized Cyclopentene Framework
  作者：Chung-Chang Lin、Tse-Min Teng、Arjan Odedra、Rai-Shung Liu

  DOI：10.1021/ja069171f

  日期：2007.4.1

  We report a new gold-catalyzed deoxygenated cyclization of cis-2,4-dien-1-als with external nucleophiles at ambient temperatures, which leads to a 1,4-double nucleophilic addition to the newly formed cyclopentene ring. The use of this cyclization is reflected not only by its compatibility with a wide scope of nucleophiles, but also by a facile construction of complex frameworks in diversified approaches

  我们报告了一种新的金催化脱氧环化 cis-2,4-dien-1-als 与外部亲核试剂在环境温度下，导致 1,4-双亲核加成到新形成的环戊烯环。这种环化的使用不仅体现在它与范围广泛的亲核试剂的兼容性上，还体现在以多种方法轻松构建复杂框架。
• Gold-Catalyzed Deoxygenative Nazarov Cyclization of 2,4-Dien-1-als for Stereoselective Synthesis of Highly Substituted Cyclopentenes
  作者：Chung-Chang Lin、Tse-Min Teng、Chung-Chih Tsai、Hsin-Yi Liao、Rai-Shung Liu

  DOI：10.1021/ja806415t

  日期：2008.12.3

  annulation products reveals evidence for the participation of Nazarov cyclization. This deoxygenative cyclization is extensible to a tandem intramolecular cyclization/nucleophilic addition cascade, giving polycyclic carbo- or oxacyclic compounds with controlled stereochemistry. This new gold catalysis is applied to a short synthesis of natural compounds of the brazilane family, including brazilane, O-trimethyl-

  用烯丙基硅烷和 PPh(3)AuSbF(6) (3 mol %) 处理 2,4-dien-1-als 导致形成 1,4-双（烯丙基）环戊烯基产物；根据催化剂筛选，这种金催化剂优于常用的路易斯酸。这种金催化的脱氧环化反应与各种基于氧、胺、硫、氢和碳的亲核试剂相容。2,4-dien-1-als 与富电子烯烃和芳烃的多种环化证明了这种新催化的价值，提供了对复杂环戊烯骨架的轻松访问。环化产物的结构分析揭示了 Nazarov 环化参与的证据。这种脱氧环化可扩展为串联的分子内环化/亲核加成级联，得到具有受控立体化学的多环碳或氧杂环化合物。这种新的金催化应用于巴西烷家族天然化合物的短程合成，包括巴西烷、O-三甲基巴西烷和 O-四甲基巴西烷。
• DETERGENT COMPOSITIONS COMPRISING PRO-FRAGRANCE COMPOUND
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0888442A1

  公开（公告）日：1999-01-07
• DELIVERY SYSTEM HAVING RELEASE BARRIER LOADED ZEOLITE
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0888430B1

  公开（公告）日：2004-02-11
• [EN] DETERGENT COMPOSITIONS COMPRISING PRO-FRAGRANCE COMPOUND<br/>[FR] COMPOSITIONS DETERGENTES COMPRENANT UN COMPOSE PRECURSEUR DE PARFUM
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：WO1997034989A1

  公开（公告）日：1997-09-25

  (EN) The present invention is directed to a detergent composition comprising a pro-fragrance compound selected from the group consisting of an acetal, a ketal, and mixtures thereof, wherein at least one of a parent aldehyde, ketone, or alcohol of the pro-fragrance acetal or ketal is a fragrance compound, the pro-fragrance compound having a CLogP of less than about 4, wherein the detergent composition has a pH of at least 7.1 when measured as a 1 % solution in distilled water at 20 °C, and a detersive surfactant.(FR) L'invention concerne une composition détergente comprenant un composé précurseur de parfum sélectionné dans le groupe constitué par un acétal, un cétal et leurs mélanges, au moins un d'un aldéhyde, d'un cétone ou d'un alcool parents de l'acétal ou du cétal précurseurs de parfum étant un composé de parfum, le composé précurseur de parfum possédant un CLogP inférieur à environ 4, la composition détergente possédant un pH d'au moins 7,1 quand elle est mesurée en tant que solution à 1 % dans de l'eau distillée à 20 °C, et un tensioactif détersif.