(11S)-3-oxo-4βH,5α-eudesman-13-oic acid | 75465-00-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (11S)-3-oxo-4βH,5α-eudesman-13-oic acid
• 英文别名: (-)-2-(1,2,3,4,4a,5,6,7,8,8aα-decahydro-4aβ,8α-dimethyl-7-oxo-2β-naphthyl)propionic acid；(11S)-3-oxo-4βH-eudesman-12-oic acid；(11S)-3-Oxo-4βH-eudesman-12-saeure；(2S)-2-[(2R,4aS,8S,8aS)-4a,8-dimethyl-7-oxo-1,2,3,4,5,6,8,8a-octahydronaphthalen-2-yl]propanoic acid
• CAS: 75465-00-8
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: WXRFPOURRUGJGZ-HJHSNUOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  山道年 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (11S)-3-oxo-4βH,5α-eudesman-13-oic acid
  参考文献：
  名称：

  The Total Syntheses of Chamaecynone, Isochamaecynone, and Dihydroisochamaecynone

  摘要：

  从α-山道年出发，合成了一种新型炔类去甲倍半萜化合物chamaecynone及其相关天然产物isochamaecynone和dihydroisochamaecynone。在三对化合物的碱诱导平衡反应中，chamaecynone和isochamaecynone，4βH,5β-13-noreudesm-11-yn-3-one和4αH,5β-13-noreudesm-11-yn-3-one，以及4βH,5β-13-noreudesm-11-en-3-one和4αH,5β-13-noreudesm-11-en-3-one的ΔH值分别确定为+1.47 kcal/mol，+0.77 kcal/mol和-2.28 kcal/mol。

  DOI：

  10.1246/bcsj.53.1425

文献信息

• (–)-2-(1,2,3,4,4a,5,6,7,8,8aα-Decahydro-4aβ,8α-dimethyl-7-oxo-2β-naphthyl)propionic acid: catemeric hydrogen bonding in a bicyclic sesquiterpenoid ζ-keto acid
  作者：Hugh W. Thompson、Roger A. Lalancette

  DOI：10.1107/s0108270103018997

  日期：2003.10.15

  In the title compound, C15H24O3, derived from a naturally occurring sesquiterpenoid, the asymmetric unit consists of two molecules differing by 167.4 (8)degrees in the rotational conformation of the carboxyl group. Each molecule aggregates separately with its own type as carboxyl-to-ketone hydrogen-bonding catemers [O...O = 2.715 (6) and 2.772 (6) Angstrom, and O-H...O = 169 and 168degrees]. This generates two crystallographically independent single-strand hydrogen-bonding helices passing through the cell in the b direction, with opposite end-to-end orientations. One intermolecular C-H...O=C close contact exists for the carboxyl group of one of the molecules. The structure is isostructural with that of a closely related unsaturated keto acid reported previously.