(1S,4R)-3-benzenesulfonyl-4-tert-butylcyclohex-2-enol | 474023-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,4R)-3-benzenesulfonyl-4-tert-butylcyclohex-2-enol
• 英文别名: (1S,4R)-3-(benzenesulfonyl)-4-tert-butylcyclohex-2-en-1-ol
• CAS: 474023-18-2
• 化学式: C₁₆H₂₂O₃S
• 分子量: 294.415
• InChiKey: AFRPGGFHOHDAKD-JSGCOSHPSA-N

物化性质

• 沸点：
  467.8±45.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4R)-3-benzenesulfonyl-4-tert-butylcyclohex-2-enol 在 氢氧化钾 、 叔丁基锂 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 15.42h， 生成 (S)-4-tert-butylcyclohex-2-enone
  参考文献：
  名称：

  Syntheses of Highly Substituted Enantiopure C6 and C7 Enones¹

  摘要：

  Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophiles to SS-9a, SS-9b is high yielding and stereospecific. Enantiopure alpha,beta- and gamma-substituted cycloalkenones are easily constructed using a variety of methods.

  DOI：

  10.1021/ja026760m
• 作为产物：
  描述：

  叔丁基锂 、 (1S,6S)-2-Benzenesulfonyl-7-oxa-bicyclo[4.1.0]hept-2-ene 在 CuCN 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (1S,4R)-3-benzenesulfonyl-4-tert-butylcyclohex-2-enol
  参考文献：
  名称：

  Syntheses of Highly Substituted Enantiopure C6 and C7 Enones¹

  摘要：

  Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophiles to SS-9a, SS-9b is high yielding and stereospecific. Enantiopure alpha,beta- and gamma-substituted cycloalkenones are easily constructed using a variety of methods.

  DOI：

  10.1021/ja026760m

文献信息

• Chemical synthons and intermediates
  申请人：——

  公开号：US20040138485A1

  公开（公告）日：2004-07-15

  The invention provides novel six and seven-carbon termini-differentiated polypropionate stereotetrads and stereopentads useful in syntheses of natural products. The invention also provides a novel alkylative sulfenylation-desulfonylation process that efficiently transforms enantiopure epoxyvinyl sulfones to syn and anti dienylsulfides in two operations.

  这项发明提供了新颖的六碳和七碳末端差异化的聚丙酸酯立体四聚体和立体五聚体，可用于合成天然产物。该发明还提供了一种新颖的烷基化磺化-去磺化过程，能够高效地将对映纯环氧乙烯基磺酮转化为syn和anti二烯基硫醚，只需两步操作。
• US7501535B2
  申请人：——

  公开号：US7501535B2

  公开（公告）日：2009-03-10
• Syntheses of Highly Substituted Enantiopure C6 and C7 Enones¹
  作者：Jerry Evarts、Eduardo Torres、Philip L. Fuchs

  DOI：10.1021/ja026760m

  日期：2002.9.1

  Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophiles to SS-9a, SS-9b is high yielding and stereospecific. Enantiopure alpha,beta- and gamma-substituted cycloalkenones are easily constructed using a variety of methods.