(1R,5R)-1-(4-methylphenylsulfonyl)bicyclo[3.1.0]hexan-2-one | 923001-91-6

• 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: (1R,5R)-1-(4-methylphenylsulfonyl)bicyclo[3.1.0]hexan-2-one
• 英文别名: (1R,5R)-1-(4-Methylbenzene-1-sulfonyl)bicyclo[3.1.0]hexan-2-one；(1R,5R)-1-(4-methylphenyl)sulfonylbicyclo[3.1.0]hexan-2-one
• CAS: 923001-91-6
• 化学式: C₁₃H₁₄O₃S
• 分子量: 250.318
• InChiKey: RBVPDBLKTFECEV-ZWNOBZJWSA-N

物化性质

• 熔点：
  96-98 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• 沸点：
  448.7±45.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,5R)-1-(4-methylphenylsulfonyl)bicyclo[3.1.0]hexan-2-one 、 氰化钠 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Studies on the structure–enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group

  摘要：

  This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of alpha-diazo-beta-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the alpha-diazo-beta-keto sulfones was varied by the position of a methyl group on the pheny] group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95% yield with 93% ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened P-keto sulfone derivative 15h provides the C-alkylated product as a major product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.046
• 作为产物：
  描述：

  对甲砜基甲苯 在 (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole] 、 正丁基锂 、 对甲苯磺酰叠氮 、 copper(I) trifluoromethanesulfonate benzene 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 19.5h， 生成 (1R,5R)-1-(4-methylphenylsulfonyl)bicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Studies on the structure–enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group

  摘要：

  This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of alpha-diazo-beta-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the alpha-diazo-beta-keto sulfones was varied by the position of a methyl group on the pheny] group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95% yield with 93% ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened P-keto sulfone derivative 15h provides the C-alkylated product as a major product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.046

文献信息

• DNA-based asymmetric organometallic catalysis in water
  作者：Jens Oelerich、Gerard Roelfes

  DOI：10.1039/c3sc00100h

  日期：——

  Here, the first examples of DNA-based organometallic catalysis in water that give rise to high enantioselectivities are described. Copper complexes of strongly intercalating ligands were found to enable the asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfones in water. Up to 84% ee was achieved, in the presence of salmon testes DNA as the only source of chirality, using dipyrido[3

  在这里，第一个基于DNA的有机金属催化实例 水描述了引起高对映选择性的化合物。发现强嵌入配体的铜配合物使α-重氮-β-酮砜的不对称分子内环丙烷化成为可能。水。使用双吡啶并[3,2- a：2'，3'- c ]吩嗪（dppz）衍生物作为配体，在鲑鱼睾丸DNA作为唯一手性来源的情况下，达到了高达84％的ee 。
• Studies on the structure–enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group
  作者：Hiroyuki Takeda、Masahisa Nakada

  DOI：10.1016/j.tetasy.2006.10.046

  日期：2006.11

  This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of alpha-diazo-beta-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the alpha-diazo-beta-keto sulfones was varied by the position of a methyl group on the pheny] group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95% yield with 93% ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened P-keto sulfone derivative 15h provides the C-alkylated product as a major product. (c) 2006 Elsevier Ltd. All rights reserved.