(+/-)-methyl trans-2-hydroxy-cyclopentane-1-acetate | 96293-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-methyl trans-2-hydroxy-cyclopentane-1-acetate
• 英文别名: methyl (1RS,2SR)-2-(2-hydroxycyclopentyl)acetate；Methyl trans-(2-hydroxycyclopentyl)acetate；(+/-)-(trans-2-hydroxy-cyclopentyl)-acetic acid methyl ester；(+/-)-(trans-2-Hydroxy-cyclopentyl)-essigsaeure-methylester；methyl 2-[(1R,2S)-2-hydroxycyclopentyl]acetate
• CAS: 96293-31-1
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: ZPDFIJDWUHBDTG-RQJHMYQMSA-N

物化性质

• 沸点：
  229.7±13.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl trans-2-hydroxy-cyclopentane-1-acetate 在 乙醇 、 sodium 作用下， 生成 (+/-)-trans-2-(2-hydroxyethyl)cyclopentanol
  参考文献：
  名称：

  Hueckel; Gelmroth, Justus Liebigs Annalen der Chemie, 1934, vol. 514, p. 233,245

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-7-氧代庚-2-烯酸甲酯 在 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(+/-)-methyl trans-2-hydroxy-cyclopentane-1-acetate
  参考文献：
  名称：

  Aldehyde–alkene cyclizations via O-stannyl ketyl radicals using sugars as chiral auxiliaries

  摘要：

  This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for aldehyde-alkene radical cyclizations. Diastereomeric ratios as high as 9:1 were achieved with an ester-appended (+)-isosorbide and 100:1 for (+)-isomannide. Temperature dependence, Lewis acids and solvents were all examined. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.006

文献信息

• A Facile Access to (<i>R</i>)-Methyl 2-Oxocyclopentane-1-acetate<i>via</i>Lipase-Catalyzed Irreversible Transesterification
  作者：Shun-ichi Hashimoto、Yoji Miyazaki、Shiro Ikegami

  DOI：10.1080/00397919208021673

  日期：1992.9

  Abstract A highly efficient kinetic resolution of (±)-methyl trans-2-hydroxycyclopentane-1-acetate via lipase PS-catalyzed irreversible transesterification provides a facile and economical entry to (R)-methyl 2-oxocyclopentane-1-acetate of 96% ee, a starting material for the convergent synthesis of (+)-isocarbacyclin.

  摘要 通过脂肪酶 PS 催化的不可逆酯交换对 (±)-甲基反式-2-羟基环戊烷-1-乙酸酯进行高效的动力学拆分，为 (R)-甲基 2-氧代环戊烷-1-乙酸酯提供了 96% 的简便且经济的进入ee，(+)-异碳环素收敛合成的起始材料。
• An Efficient and Enantioselective Approach to the Azaspirocyclic Core of Alkaloids:  Formal Synthesis of Halichlorine and Pinnaic Acid
  作者：Hong-Lu Zhang、Gang Zhao、Yu Ding、Bin Wu

  DOI：10.1021/jo047882v

  日期：2005.6.1

  A novel, highly stereoselective synthesis of an azaspirocyclic core, which contains four stereogenic carbons consistent with structures of natural halichlorine and pinnaic acid, is presented. Lipase PS-catalyzed selective acylation, asymmetric methylation on the α-methylene of the bicyclic lactone, and an asymmetric Michael addition of the tertiary nitro cyclopentane were concisely used to conquer

  提出了一种新颖的，高度立体选择性的氮杂螺环核心合成，该核心含有四个与自然盐酸盐和松果酸结构一致的立体碳。脂肪酶PS催化的选择性酰化，双环内酯的α-亚甲基上的不对称甲基化以及叔硝基环戊烷的不对称Michael加成反应，可以解决成功构建具有完全立体控制的C9季碳中心的难题。螺哌啶环的形成是通过还原δ-硝基酮，分子内缩合，然后用NaBH 4高度立体选择性地还原环硝酮。这个螺环核心是Danishefsky合成频烷酸和盐酸的关键中间体。
• Lanthanide induced intramolecular coupling of aldehydes and ketones with electron-deficient olefins
  作者：Eric J. Enholm、Antigone Trivellas

  DOI：10.1016/s0040-4039(01)80359-2

  日期：1989.1

  Aldehydes or ketones with a δ,ε-olefin bearing a conjugating electron-withdrawing group undergo reductive cyclization with samarium iodide to afford five-membered rings. Diastereoselectivities of > 250:1 have been obtained.

  带有带有共轭吸电子基团的δ，ε-烯烃的醛或酮与碘化sa进行还原环化反应，得到五元环。获得了> 250：1的非对映选择性。
• Synthesis of (R)-6,7-dihydro-5-HETE lactone and (S)-6,7-dihydro-5-HETE lactone by using novel yeast reduction as a key reaction
  作者：Satoshi Yamauchi、Kenji Takeda、Makoto Ganaha、Yoshiro Kinoshita

  DOI：10.1039/b206843p

  日期：2002.10.1

  Novel yeast reduction which gave (1R,2S)-hydroxy ester 10 and (1S,5S)-lactone 11 from racemic ketoester 12 was discovered. After 10 and 11 were converted to lactone 15 and 17, enantiomeric excesses were determined as 99% and 95%, respectively. This novel yeast reduction was applied to synthetic study of metabolites of 5-oxo-ETE 1. (R)-6,7-Dihydro-5-HETE lactone 5 and (S)-6,7-dihydro-5-HETE lactone 6 were synthesized from 15 and 17, respectively.

  新发现的酵母还原法可从外消旋酮酯 12 中得到（1R,2S）-羟基酯 10 和（1S,5S）-内酯 11。10 和 11 转化为内酯 15 和 17 后，对映体过量率分别为 99% 和 95%。(R)-6,7-Dihydro-5-HETE lactone 5 和 (S)-6,7-Dihydro-5-HETE lactone 6 分别由 15 和 17 合成。
• Syntheses of All Stereoisomers of Goniodiol from Yeast-Reduction Products and Their Antimicrobiological Activity
  作者：Takahiro YOSHIDA、Satoshi YAMAUCHI、Ryosuke TAGO、Masafumi MARUYAMA、Koichi AKIYAMA、Takuya SUGAHARA、Taro KISHIDA、Yojiro KOBA

  DOI：10.1271/bbb.80262

  日期：2008.9.23

  All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mm) against Yersinia intermedia.

  贡碘醇的所有立体异构体都是由酵母还原产物合成的。C-6 手性中心由酵母还原产物的手性中心转化而来。由酵母还原产物制备的烯烃立体选择性地转化为乙二醇，构建了 C-7 和 C-8 立体化学结构。(+)-冈碘二醇和 7-表-(+)-冈碘二醇对中间耶尔森菌的抗菌活性最高（MIC，3.1 毫米）。