(S)-1,4,7,10-Tetraoxacyclododecane-2-methanol | 75507-26-5

• 物质功能分类: 化学试剂 - 有机试剂 - 冠醚
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1,4,7,10-Tetraoxacyclododecane-2-methanol
• 英文别名: [(2S)-1,4,7,10-tetraoxacyclododec-2-yl]methanol
• CAS: 75507-26-5
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: NJIPEIQHUNDGPY-VIFPVBQESA-N

物化性质

• 沸点：
  115 °C/0.04 mmHg (lit.)
• 密度：
  1.192 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2932999099
• 危险品运输编号：
  UN 2810 6.1/PG 3

反应信息

• 作为反应物：
  描述：

  (S)-1,4,7,10-Tetraoxacyclododecane-2-methanol 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (R)-1,4,7,10-Tetraoxacyclododecane-2-methyl acetate
  参考文献：
  名称：

  Lipase-Catalyzed Hydrolysis of Crowned Ester Substrates: Metal Cation-Enhanced Reactivity and Enantioselectivity of 12-Crown-4 Ester

  摘要：

  Lipase from Pseudomonas cepacia was first applied in hydrolysis of ester substrates which had crown ether, azacrown, and acyclic polyether moieties as cation binding sites. The reaction behaviors of these crowned ester substrates were changed by addition of alkali metal salts. In particular, 12-crown-4 ester offered enhanced reactivity and enantioselectivity in the presence of sodium salt. FAB MS, C-13 NMR, and computational studies revealed that the ester formed a diastereomeric complex in which Na+ cation was sandwiched between two chiral crowned substrates. The lipase reaction was effectively controlled by ''host-guest chemistry'' of the crowned ester substrate.

  DOI：

  10.1021/jo00102a027
• 作为产物：
  描述：

  1,4,7,10-Tetraoxacyclododecane-2-methyl acetate 在 sodium chloride 作用下， 反应 6.0h， 生成 (R)-1,4,7,10-Tetraoxacyclododecane-2-methanol 、 (S)-1,4,7,10-Tetraoxacyclododecane-2-methanol
  参考文献：
  名称：

  Enhanced reactivity and enantioselectivity in lipase-catalysed hydrolysis of 12-crown-4 ester via crown ether–metal complexation

  摘要：

  Lipase from Pseudomonas was first demonstrated to catalyse hydrolysis of a crown ether ester derivative; reaction rate and enantioselectivity are significantly enhanced by crown ether–metal complexation.

  DOI：

  10.1039/c39920001751

文献信息

• Chiral crown ethers
  申请人：MILES INC.

  公开号：EP0306802B1

  公开（公告）日：1991-05-15
• JPH05202025A
  申请人：——

  公开号：JPH05202025A

  公开（公告）日：1993-08-10
• US5047563A
  申请人：——

  公开号：US5047563A

  公开（公告）日：1991-09-10
• US5133934A
  申请人：——

  公开号：US5133934A

  公开（公告）日：1992-07-28
• Lipase-Catalyzed Hydrolysis of Crowned Ester Substrates: Metal Cation-Enhanced Reactivity and Enantioselectivity of 12-Crown-4 Ester
  作者：Hiroshi Tsukube、Akio Betchaku、Yuji Hiyama、Toshiyuki Itoh

  DOI：10.1021/jo00102a027

  日期：1994.11

  Lipase from Pseudomonas cepacia was first applied in hydrolysis of ester substrates which had crown ether, azacrown, and acyclic polyether moieties as cation binding sites. The reaction behaviors of these crowned ester substrates were changed by addition of alkali metal salts. In particular, 12-crown-4 ester offered enhanced reactivity and enantioselectivity in the presence of sodium salt. FAB MS, C-13 NMR, and computational studies revealed that the ester formed a diastereomeric complex in which Na+ cation was sandwiched between two chiral crowned substrates. The lipase reaction was effectively controlled by ''host-guest chemistry'' of the crowned ester substrate.