(4R,5S)-trans-crobarbatic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5S)-trans-crobarbatic acid
• 英文别名: (-)-crobarbatic acid；(2S,3R)-2,3-dimethyl-5-oxooxolane-2-carboxylic acid
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: YZSAAFPSSTZXMN-FBCQKBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenylmagnesium bromide 、 (4R,5S)-trans-crobarbatic acid 生成 2-Hydroxy-2.3-dimethyl-5.5-diphenyl-penten-(4)-saeure-(1)
  参考文献：
  名称：

  THE STEREOCHEMISTRY OF JACOBINE

  摘要：

  DOI：

  10.1021/ja01504a067
• 作为产物：
  描述：

  3-甲基-2-糠酸 在 Rh on carbon chromium(VI) oxide 、 盐酸 、 sodium hydroxide 、 氯化亚砜 、 硫酸 、 氨 、 氢气 、 sodium 、 溶剂黄146 、 天然橡胶 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 8.17h， 生成 (4R,5S)-trans-crobarbatic acid
  参考文献：
  名称：

  The synthesis of (−)-cis- and (−)-trans-crobarbatic acid

  摘要：

  The synthesis of both cis- and trans-crobarbatic acid is reported. The five-step sequence proceeds in high yield and with control of both relative and absolute stereochemistry. The key step in the synthesis is the Birch reductive alkylation of a chiral furoic acid which sets the absolute stereochemistry of the products. The stereochemistry of the compounds described was proven unambiguously by X-ray crystallography on one synthetic intermediate and on trans-crobarbatic acid. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00097-x

文献信息

• Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones including whisky and cognac lactones and crobarbatic acid
  作者：Alan Armstrong、Cassim Ashraff、Hunsuk Chung、Lorraine Murtagh

  DOI：10.1016/j.tet.2009.04.013

  日期：2009.6

  Oxidation of 2-alkoxy-3,4-dihydro-2H-pyrans 3 with dimethyldioxirane or MTO/urea–H2O2 followed by Jones oxidation leads to rearrangement and stereocontrolled formation of 4,5-cis-disubstituted tetrahydrofuranones. The method is applied to the synthesis of the whisky lactone 9, cognac lactone 10 and crobarbatic acid 17.

  用二甲基二环氧乙烷或MTO /脲-H 2 O 2氧化2-烷氧基-3,4-二氢-2 H-吡喃3，然后进行琼斯氧化，导致4,5-顺式-二取代的四氢呋喃酮的重排和立体形成。该方法适用于威士忌内酯9，白兰地内酯10和巴巴果酸17的合成。
• Anodic cyclization reactions and the synthesis of (−)-crobarbatic acid
  作者：Hai-Chao Xu、John D. Brandt、Kevin D. Moeller

  DOI：10.1016/j.tetlet.2008.04.075

  日期：2008.6

  A synthesis of (−)-crobarbatic acid is reported along with the first use of a vinyl-substituted ketene dithioacetal as a coupling partner for an anodic cyclization reaction. The use of the vinyl-substituted ketene dithioacetal enables the construction of a cyclic product having a tetrasubstituted carbon with a relative stereochemistry opposite to that originally obtained from the cyclization.

  报道了（-）-crobarbatic酸的合成，以及首次使用乙烯基取代的乙烯酮二硫缩醛作为阳极环化反应的偶联伴侣。乙烯基取代的烯酮二硫缩醛的使用使得能够构建具有四取代的碳的环状产物，其相对立体化学与最初从环化获得的立体化学相反。
• Chiral synthesis of the necic acid components, crobarbatic acid and integerrinecic acid lactone
  作者：Toshio Honda、Fumihiro Ishikawa、Shin-ichi Yamane

  DOI：10.1039/p19960001125

  日期：——

  Samarium(II) diiodide-promoted regioselective fragmentation of the γ-halogeno esters 12 and 13 afforded the olefins 14 and 20, respectively, which were converted into the necic acid components, crobarbatic acid and a known advanced intermediate of integerrinecic acid lactone, of macropyrrolizidine alkaloids.

  二碘化钐(II)促进γ-卤代酯12和13的区域选择性裂解，分别得到烯烃14和20，它们被转化为大环吡咯里西啶的neic酸组分、crobarbatic酸和已知的interinecic酸内酯的高级中间体生物碱。