(5S)-(1'-Hydroxyethyl)-2,2-cyclohexylidene-1,3-dioxolan-4-one | 153011-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S)-(1'-Hydroxyethyl)-2,2-cyclohexylidene-1,3-dioxolan-4-one
• 英文别名: (3S)-3-(2-hydroxyethyl)-1,4-dioxaspiro[4.5]decan-2-one；(5S)-(2-hydroxyethyl)-2,2-cyclohexylidene-1,3-dioxolan-4-one；(2S)-2-(2-hydroxyethyl)-1,4-dioxaspiro[4.5]decan-3-one
• CAS: 153011-58-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: QIMINWTVFLAKIK-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-(1'-Hydroxyethyl)-2,2-cyclohexylidene-1,3-dioxolan-4-one 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-(-)-α-羟基-γ-丁内酯
  参考文献：
  名称：

  First Asymmetric Total Syntheses of (−)-Subincanadines A and B, Skeletally Rearranged Pentacyclic Monoterpenoid Indole Alkaloids in Aspidosperma subincanum

  摘要：

  [GRAPHICS]We achieved the first asymmetric total syntheses of novel Aspidosperma indole alkaloids, (-)-subincanadines A and B, which involve an intramolecular diastereoselective Pictet-Spengler cyclization and an intramolecular Nozaki-Hiyama-Kishi reaction as key steps in the total syntheses.

  DOI：

  10.1021/ol061908i
• 作为产物：
  描述：

  1,4-二氧杂螺[4.5]癸烷-2-乙酸,3-羰基-,(2S)- 在 硼酸三甲酯 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 (5S)-(1'-Hydroxyethyl)-2,2-cyclohexylidene-1,3-dioxolan-4-one
  参考文献：
  名称：

  对映体纯的2,5-二取代的3-氧合四氢呋喃

  摘要：

  对映体纯的2，5-二取代的3-氧化的四氢呋喃的合成已经由廉价的和可商购的1-苹果酸实现。该方法用于制备针对CMI-977的高级中间体，CMI-977是治疗慢性哮喘的有前途的候选药物。 呋喃-四氢呋喃-单线态氧-丁烯内酯-氧环化合物-天然产物

  DOI：

  10.1055/s-0030-1258263

文献信息

• An Ammonia-Triggered Stereocontrolled Conversion of a γ-Lactone to the Central Tetrahydropyran of Pederin, Psymberin, and Onnamides D-F
  作者：William J. Buffham、Nigel A. Swain、Sarah L. Kostiuk、Théo P. Gonçalves、David C. Harrowven

  DOI：10.1002/ejoc.201101543

  日期：2012.2

  The onnamides, pederin, and psymberin have each attracted attention because of their potent biological activity and interesting structural features. A short (eight steps) and efficient stereocontrolled route to the central tetrahydropyran ring in these natural products has been developed from (S)-malic acid. The key sequence involves the conversion of a ?-lactone to a tetrahydropyran structure triggered

  onnamides、pederin 和 psymberin 均因其强大的生物活性和有趣的结构特征而备受关注。已经从 (S)-苹果酸开发了一种短（八步）且有效的立体控制路线，以到达这些天然产物中的中心四氢吡喃环。关键序列涉及通过添加氨触发β-内酯向四氢吡喃结构的转化。
• Verticilide: Elucidation of Absolute Configuration and Total Synthesis
  作者：Souichi Monma、Toshiaki Sunazuka、Kenichiro Nagai、Takahiro Arai、Kazuro Shiomi、Ryosuke Matsui、Satoshi Ōmura

  DOI：10.1021/ol0623365

  日期：2006.11.1

  24-membered cyclic depsipeptide isolated from the culture broth of Verticillium sp. FKI-1033. It inhibits ryanodine binding to ryanodine receptor (RyR) and has insecticidal activity. The stereochemistry of 2-hydroxyheptanoic acid in verticilide was elucidated by chiral HPLC analysis of the degradation product 6 and synthetic (+) and (-)-6. We also describe the practical total synthesis of verticilide. [reaction:

  Verticilide（1）是从Verticillium sp。的培养液中分离得到的24元环状二肽。FKI-1033。它抑制了雷诺定与雷诺定受体（RyR）的结合，并具有杀虫活性。通过手性HPLC分析降解产物6以及合成的（+）和（-）-6，阐明了旋苯环内酯中2-羟基庚酸的立体化学。我们还描述了切实可行的全合成verticilide。[反应：请参见文字]。
• Total synthesis of (-)-tetrahydrolipstatin
  作者：Stephen Hanessian、Ashok Tehim、Ping Chen

  DOI：10.1021/jo00079a022

  日期：1993.12

  The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain-extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91 % ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38 % overall yield.
• Lasonolide A:  Structural Revision and Total Synthesis
  作者：Ho Young Song、Jung Min Joo、Jung Won Kang、Dae-Shik Kim、Cheol-Kyu Jung、Hyo Shin Kwak、Jin Hyun Park、Eun Lee、Chang Yong Hong、ShinWu Jeong、Kiwan Jeon、Ji Hyun Park

  DOI：10.1021/jo034930n

  日期：2003.10.1

  The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of beta-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantiomers of a revised structure featuring 17E,25Z double bonds were synthesized, and the (-)-isomer was found to be the biologically active enantiomer.
• Syntheses of (−)-Epothilone B
  作者：Dieter Schinzer、Armin Bauer、Jennifer Schieber

  DOI：10.1002/(sici)1521-3765(19990903)5:9<2492::aid-chem2492>3.0.co;2-r

  日期：1999.9.3