9H-fluoren-9-ylmethyl N-(2-cyclohexa-1,5-dien-1-ylethyl)-N-(4-methylphenyl)sulfonylcarbamate | 857335-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-(2-cyclohexa-1,5-dien-1-ylethyl)-N-(4-methylphenyl)sulfonylcarbamate
• CAS: 857335-05-8
• 化学式: C₃₀H₂₉NO₄S
• 分子量: 499.631
• InChiKey: IUTDACRVQWGHFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-(2-cyclohexa-1,5-dien-1-ylethyl)-N-(4-methylphenyl)sulfonylcarbamate 在 palladium diacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 对苯醌 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 Acetic acid (1S,4R)-4-chloro-3-[2-(toluene-4-sulfonylamino)-ethyl]-cyclohex-2-enyl ester
  参考文献：
  名称：

  Synthesis of 1,3-cyclohexadienes by tandem diene–alkyne metathesis: improved procedure

  摘要：

  A practical synthesis of 2-substituted 1,3-cyclohexadienes by the cross enyne metathesis between alkynes and 1,5-hexadiene is reported. The isolation of the 1,3-cyclohexadienes has been hampered by the formation of an inseparable triene by-product. The use of a second consecutive cross alkene metathesis to give water-soluble products allowed removal of this by-product. Using this one-pot procedure, a synthesis of cyclohexadienes from simple starting materials was developed. The procedure was used in a three-step synthesis of a functionalized tetrahydroquinoline using Pd(II)-catalyzed chloroacetoxyiation (Backvall reaction) for cyclohexadiene functionalization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.017
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl N-but-3-ynyl-N-(4-methylphenyl)sulfonylcarbamate 、 1,5-已二烯 在 dichloro(o-isporopoxyphenylmethylene)(triphenylphosphine)ruthenium(II) 、 丙烯酸 作用下， 以 二氯甲烷 为溶剂， 以37%的产率得到9H-fluoren-9-ylmethyl N-(2-cyclohexa-1,5-dien-1-ylethyl)-N-(4-methylphenyl)sulfonylcarbamate
  参考文献：
  名称：

  Synthesis of 1,3-cyclohexadienes by tandem diene–alkyne metathesis: improved procedure

  摘要：

  A practical synthesis of 2-substituted 1,3-cyclohexadienes by the cross enyne metathesis between alkynes and 1,5-hexadiene is reported. The isolation of the 1,3-cyclohexadienes has been hampered by the formation of an inseparable triene by-product. The use of a second consecutive cross alkene metathesis to give water-soluble products allowed removal of this by-product. Using this one-pot procedure, a synthesis of cyclohexadienes from simple starting materials was developed. The procedure was used in a three-step synthesis of a functionalized tetrahydroquinoline using Pd(II)-catalyzed chloroacetoxyiation (Backvall reaction) for cyclohexadiene functionalization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.017