(+)-(R)-2-chlorohept-6-enal | 1449490-39-4

• 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: (+)-(R)-2-chlorohept-6-enal
• 英文别名: (2R)-2-chlorohept-6-enal
• CAS: 1449490-39-4
• 化学式: C₇H₁₁ClO
• 分子量: 146.617
• InChiKey: DEKUBRFFPQRSTH-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (+)-(R)-2-chlorohept-6-enal 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 2.28h， 生成 (5R)-5-[(1S,2R)-2-chloro-1-hydroxyhept-6-enyl]imidazolidine-2,4-dione
  参考文献：
  名称：

  Total Synthesis of the Cytotoxic Anhydrophytosphingosine Pachastrissamine (Jaspine B)

  摘要：

  A short, 8-step synthesis of the marine natural product pachastrissamine has been developed that relies on a diastereoselective aldol reaction between a suitably protected hydantoin and an optically enriched alpha-chloroaldehyde. This synthetic route provides new opportunities for exploring structure activity relationships within this family of natural products.

  DOI：

  10.1021/jo4013223
• 作为产物：
  描述：

  1-烯庚醛 在 sodium persulfate 、 (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate 、 水 、 Cu(TFA)₂*xH₂O 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以60%的产率得到(+)-(R)-2-chlorohept-6-enal
  参考文献：
  名称：

  Total Synthesis of the Cytotoxic Anhydrophytosphingosine Pachastrissamine (Jaspine B)

  摘要：

  A short, 8-step synthesis of the marine natural product pachastrissamine has been developed that relies on a diastereoselective aldol reaction between a suitably protected hydantoin and an optically enriched alpha-chloroaldehyde. This synthetic route provides new opportunities for exploring structure activity relationships within this family of natural products.

  DOI：

  10.1021/jo4013223

文献信息

• [EN] COMPOUNDS AND PROCESSES FOR THE PREPARATION OF ERIBULIN<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LA PRÉPARATION D'ÉRIBULINE
  申请人：[en]SIMON FRASER UNIVERSITY

  公开号：WO2023144733A1

  公开（公告）日：2023-08-03

  The present invention relates to compounds and a process for the preparation of eribulin. More specifically, the process to prepare the C14- C35 sulfone fragment of eribulin (i.e. compounds of formula I) by reacting a C14-C26 ketone fragment of eribulin (i.e. compounds of formula II) with a C27-C35 sulfonium salt fragment (i.e. compounds of formula III) under Corey-Chaykovsky reaction conditions is explored. The processes to prepare the intermediate C14-C26 ketone (i.e. compounds of formula II), the intermediate C27-C35 sulfonium salt (i.e. compounds of formula III) and the intermediate C27-C35 aldehyde (i.e. compounds of formula IV) arc also disclosed.
• Total Synthesis of the Cytotoxic Anhydrophytosphingosine Pachastrissamine (Jaspine B)
  作者：Vijay Dhand、Stanley Chang、Robert Britton

  DOI：10.1021/jo4013223

  日期：2013.8.16

  A short, 8-step synthesis of the marine natural product pachastrissamine has been developed that relies on a diastereoselective aldol reaction between a suitably protected hydantoin and an optically enriched alpha-chloroaldehyde. This synthetic route provides new opportunities for exploring structure activity relationships within this family of natural products.