4-heptenyl chloride | 70732-49-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 4-heptenyl chloride
• 英文别名: (Z)-1-chlorohept-4-ene；cis-4-heptenyl chloride；7-Chlor-cis-3-hepten；7-chloro-hept-3c-ene；(Z)-7-chlorohept-3-ene
• CAS: 70732-49-9
• 化学式: C₇H₁₃Cl
• 分子量: 132.633
• InChiKey: SLNKHNQXBZBFQD-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-heptenyl chloride 以95%的产率得到
  参考文献：
  名称：

  DEJARLAIS W. J.; EMKEN E. A., J. LABELLED COMPOUNDS AND RADIOPHARM., 1978, 15, 451-460

  摘要：

  DOI：
• 作为产物：
  描述：

  7-氯-3-庚炔 在 Lindlar's catalyst 氢气 作用下， 生成 4-heptenyl chloride
  参考文献：
  名称：

  二、四和六氘化 11-十八碳烯酸酯的合成

  摘要：

  11-十八碳烯酸-15、16-d2、-15、15、16、16-d4 和-10、10、15、15、16、16-d6 酸的甲酯通过 Wittig 合成从衍生自 11 的中间体制备-溴十一烷酸和 7-氯-3-庚炔。二氘酸通过庚炔的部分氢化，然后用氘饱和为 1-氯庚烷-4, 5-d2 来制备，用于 Wittig 合成。庚炔与氘的饱和提供了四氘酸的 Wittig 中间体。六氘酸由四氘代烷基卤化物和 10-甲酰基癸酸酯-10, 10-d2 制备。

  DOI：

  10.1002/jlcr.2580150151

文献信息

• A novel photoinduced reduction system of low-valent samarium species: reduction of organic halides and chalcogenides, and its application to carbonylation with carbon monoxide
  作者：Yukihito Sumino、Nami Harato、Yuri Tomisaka、Akiya Ogawa

  DOI：10.1016/j.tet.2003.08.070

  日期：2003.12

  irradiation is found to enhance the reducing ability of samarium diiodide (SmI2) dramatically. Organic halides (RCl, RBr, RI) and chalcogenides (RSPh, RSePh, RTePh) are smoothly reduced to the corresponding hydrocarbons by using this SmI2–hv system. The photoactivation can be also applied to ytterbium diiodide (YbI2) successfully. When the reduction of alkyl chlorides (RCl) by using the SmI2–hv system is conducted

  发现可见光照射可显着增强二碘化sa（SmI 2）的还原能力。通过使用此SmI 2 - hv系统，有机卤化物（RCl，RBr，RI）和硫族化物（RSPh，RSePh，RTePh）可以平滑地还原为相应的烃。光活化也可以成功地应用于二碘化（（YbI 2）。当在一氧化碳的压力下使用SmI 2 - hv系统还原烷基氯化物（RCl）时，会获得不对称的酮（RC（O）CH 2 R）作为羰基化产物。机械途径可能涉及酰基sa物种（RC（O）SmI 2），然后进行二聚化，然后用SmI 2还原，得到不对称的酮。
• Photoinduced Reduction and Carbonylation of Organic Chlorides with Samarium Diiodide
  作者：Akiya Ogawa、Yukihito Sumino、Taizoh Nanke、Syoji Ohya、Noboru Sonoda、Toshikazu Hirao

  DOI：10.1021/ja963117p

  日期：1997.3.1
• Enantioselective total syntheses of indolizidine alkaloids (-)-205A and (-)-235B
  作者：Richard P. Polniaszek、Stephen E. Belmont

  DOI：10.1021/jo00016a013

  日期：1991.8

  Enantioselective total syntheses of indolizidine alkaloids (-)-205A and (-)-235B are described. The syntheses proceed via a common late-stage intermediate, alpha-aminonitrile 1. Absolute stereochemical control over the C8 and C8a stereocenters in these materials was achieved by a stereoselective crotylation reaction between chiral acyliminium ion (R)-3b and crotylmagnesium chloride. The selectivity of this reaction, which produced the (future)-8R,8aS configuration was complementary to the result obtained by crotylation of acyliminium ion (S)-3a with trans-crotyltrimethylsilane, which produced predominantly an adduct with the (future)-8S,8aS configuration. This latter crotyl lactam was converted to two additional diastereomers of alkaloid 205A. Comparison of the H-1 and C-13 NMR and optical rotation values of the four synthetic diastereomers of 205A with literature values supported the proposed assignment of the absolute and relative configuration of (-)-205A. The C-13 spectrum of synthetic (5R,8R,8aS)-235B was identical with that of natural 235B and supported the proposed assignment of relative configuration of the alkaloid. The optical rotation differed in sign and magnitude from the published value. Revised values of the optical rotations of (-)-205A and (-)-235B are suggested. This work constitutes the first enantioselective syntheses of 205A and 235B, which were prepared in 15 and 14 steps, respectively, from succinic anhydride, in an average overall yield of 17%.
• US7655253B2
  申请人：——

  公开号：US7655253B2

  公开（公告）日：2010-02-02