(Z)-3-iodo-2-hepten-1-al | 117499-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-iodo-2-hepten-1-al
• 英文别名: (2Z)-3-iodo-2-heptenal
• CAS: 117499-77-1
• 化学式: C₇H₁₁IO
• 分子量: 238.068
• InChiKey: ANZSFQUTTMGKSA-ALCCZGGFSA-N

物化性质

• 沸点：
  234.3±23.0 °C(Predicted)
• 密度：
  1.549±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  9.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-iodo-2-hepten-1-al 在 lithium dineopentylcuprate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 以85%的产率得到(E)-2-庚烯醛
  参考文献：
  名称：

  Direct preparation of copper organometallics bearing an aldehyde function via an iodine–copper exchange

  摘要：

  通过碘铜交换反应，可以直接制备出带有甲酰基的各种芳基、杂芳基和烯基铜酸盐，从而可以直接合成多官能团醛，而无需保护基团或额外的氧化步骤。

  DOI：

  10.1039/b604259g
• 作为产物：
  描述：

  (Z)-3-iodo-2-hepten-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (Z)-3-iodo-2-hepten-1-al
  参考文献：
  名称：

  由羰基酰胺化终止的炔烃的环状碳pal缩

  摘要：

  与含有ω-氨基的基团相比，含有ω-磺酰胺基的烯基或芳基卤化物可以更令人满意地完成经由羰基内酰胺化的炔烃的环状碳palpalpalladation。对于制备由六元环组成的稠环系统，该方法似乎是令人满意的，而其他情况则需要进一步开发。

  DOI：

  10.1016/0040-4020(96)00640-0

文献信息

• Gold-Catalyzed Waste-Free Generation and Reaction of Azomethine Ylides: Internal Redox/Dipolar Cycloaddition Cascade
  作者：Hyun-Suk Yeom、Ji-Eun Lee、Seunghoon Shin

  DOI：10.1002/anie.200802802

  日期：2008.9.1
• Acylpalladation of Internal Alkynes and Palladium-Catalyzed Carbonylation of (Z)-.beta.-Iodoenones and Related Derivatives Producing .gamma.-Lactones and .gamma.-Lactams
  作者：Christophe Coperet、Takumichi Sugihara、Guangzhong Wu、Izumi Shimoyama、Ei-ichi Negishi

  DOI：10.1021/ja00117a011

  日期：1995.3

  The reaction of either an internal alkyne-organic halide mixture or (Z)-beta-iodoenones with CO in the presence of a Pd-phosphine catalyst, e.g., Cl2Pd(PPh(3))2, can give one of the three discrete types of compounds as the major products depending on the substrate structure and the reaction conditions. Those substrates which are convertible to (Z)-gamma-oxo-alpha,beta-unsaturated acylpalladium derivatives lacking delta-H atoms are converted to the corresponding 2-butenolides (13) in the presence of water, which serves as a H donor. Carbon monoxide most likely is the source of two electrons. Either in the absence of water (or any other suitable H source) or in the presence of some factors disfavoring the butenolide formation, the same reaction gives the corresponding dimeric product (16). Even in cases where there is an alpha-H atom in the alpha-substitutent, 1,4-elimination products (11), reported to be the major products in a related Pd-catalyzed reaction of terminal alkyne-aryl iodide mixtures with CO, were not detected. In sharp contrast, those substrates which can give rise to (Z)-gamma-oxo-alpha, beta-unsaturated acylpalladium derivatives containing delta-H atoms give, under comparable reaction conditions, enol lactones (12), i.e., (Z)-3-alkylidene-2-butenolides, contaminated with only very minor amounts of 22 even in cases where an excess (4 equiv) of water was present. The required (Z)-beta-iodoenones can be readily prepared in one pot via ZrCp(2)-promoted cyclization of alkynes with nitriles. The ready availability of the starting compounds and the high Z stereoselectivity make the overall sequence an attractive synthetic route to 12. The courses of the Pd-catalyzed carbonylation reactions of (Z)-beta-iodo-alpha,beta-unsaturated imines 23 closely parallel the reactions of enones and produce the corresponding lactams, i.e., 24 and 25.
• Metal-promoted cyclization. 21. Palladium-catalyzed procedures for [3 + 2] annulation via intramolecular alkenylpalladation and arylpalladation
  作者：Yantao Zhang、Brian O'Connor、Eiichi Negishi

  DOI：10.1021/jo00258a050

  日期：1988.11