[(1S,2R)-2-(chloromethyl)cyclohexyl]methanol | 10479-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1S,2R)-2-(chloromethyl)cyclohexyl]methanol
• CAS: 10479-74-0；90435-47-5；124531-98-2
• 化学式: C₈H₁₅ClO
• 分子量: 162.66
• InChiKey: XSBZVRARMOTLSZ-JGVFFNPUSA-N

物化性质

• 沸点：
  82-83 °C(Press: 0.3 Torr)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(1S,2R)-2-(chloromethyl)cyclohexyl]methanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以85%的产率得到(1S,2R)-1-Chloromethyl-2-iodomethyl-cyclohexane
  参考文献：
  名称：

  Sequenced Reactions with Samarium(II) Iodide. Sequential Intermolecular Carbonyl Addition/Intramolecular Nucleophilic Acyl Substitution for the Preparation of Seven-, Eight-, and Nine-Membered Carbocycles

  摘要：

  Samarium(II) iodide has been employed to promote a tandem intermolecular carbonyl addition/intramolecular nucleophilic acyl substitution sequence, generating seven- through nine-membered monocyclic, bicyclic, and tricyclic ring systems with good yields and high diastereoselectivities. This tandem reaction consists of an intermolecular reaction followed by an intramolecular ring expansion that results in a formal [m + n] cycloaddition, starting from extremely simple, readily available substrates. The regioselectivity and stereoselectivity of the process arise from a tuning of the reducing power of samarium(II) iodide with nickel(II) iodide in the first step and irradiation with visible light in the second. By using this method, a variety of structural motifs have been assembled rapidly in good yields.

  DOI：

  10.1021/jo980119e
• 作为产物：
  描述：

  ethyl cis-2-(chloromethyl)cyclohexanecarboxylate 在 lithium aluminium tetrahydride 作用下， 以80%的产率得到[(1S,2R)-2-(chloromethyl)cyclohexyl]methanol
  参考文献：
  名称：

  Sequenced Reactions with Samarium(II) Iodide. Sequential Intermolecular Carbonyl Addition/Intramolecular Nucleophilic Acyl Substitution for the Preparation of Seven-, Eight-, and Nine-Membered Carbocycles

  摘要：

  Samarium(II) iodide has been employed to promote a tandem intermolecular carbonyl addition/intramolecular nucleophilic acyl substitution sequence, generating seven- through nine-membered monocyclic, bicyclic, and tricyclic ring systems with good yields and high diastereoselectivities. This tandem reaction consists of an intermolecular reaction followed by an intramolecular ring expansion that results in a formal [m + n] cycloaddition, starting from extremely simple, readily available substrates. The regioselectivity and stereoselectivity of the process arise from a tuning of the reducing power of samarium(II) iodide with nickel(II) iodide in the first step and irradiation with visible light in the second. By using this method, a variety of structural motifs have been assembled rapidly in good yields.

  DOI：

  10.1021/jo980119e

文献信息

• Kechayan, Josette; Lauricella, Robert; Davidovics, Gisele, Bulletin de la Societe Chimique de France, 1989, # 4, p. 559 - 565
  作者：Kechayan, Josette、Lauricella, Robert、Davidovics, Gisele、Bodot, Hubert

  DOI：——

  日期：——