(Z)-2-(bromomethyl)-1-iodo-1-butene | 1276539-18-4

• 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: (Z)-2-(bromomethyl)-1-iodo-1-butene
• 英文别名: (Z)-3-bromo-2-ethyl-1-iodo-1-propene；(Z)-2-(bromomethyl)-1-iodobut-1-ene
• CAS: 1276539-18-4
• 化学式: C₅H₈BrI
• 分子量: 274.927
• InChiKey: LPOPLPUWEOXEAD-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (Z)-2-(bromomethyl)-1-iodo-1-butene 、 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以327 mg的产率得到2-(2-ethyl-3-iodo-2-propenyl)-7-(phenylsulfonyl)-1,2,3,6-tetrahydroazocino[4,3-b]indole
  参考文献：
  名称：

  Synthesis of cleavamine-type indole alkaloids and their 5-nor derivatives by a ring-closing metathesis–vinyl halide Heck cyclization strategy

  摘要：

  An indole-templated RCM has been used to assemble the central medium-sized rings of the indole upper-half of vinorelbine and the cleavamine-type alkaloids. From these key intermediates, the bridged tetracyclic framework of the alkaloids is completed with the insertion of a 2-ethylpropeno unit, by N-alkylation followed by a challenging endocyclic vinyl halide Heck cyclization. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.064

文献信息

• A Straightforward Synthetic Entry to Cleavamine-Type Indole Alkaloids by a Ring-Closing Metathesis−Vinyl Halide Heck Cyclization Strategy
  作者：M.-Lluïsa Bennasar、Daniel Solé、Ester Zulaica、Sandra Alonso

  DOI：10.1021/ol200437k

  日期：2011.4.15

  An indole-templated ring-closing metathesis has been used to create the central nine-membered ring of the cleavamine-type alkaloids. A subsequent intramolecular vinyl halide Heck reaction upon the resulting azacyclononene ring completes the assembly of the strained 1-azabicyclo[6.3.1]dodecane framework of the alkaloids. The usefulness of the approach is illustrated with the synthesis of (+/-)-cleavamine and (+/-)-dihydrocleavamine.