(R)-methyl 3-(6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)propanoate | 123522-75-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-methyl 3-(6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)propanoate
• 英文别名: methyl (R)-3-(6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)propanoate
• CAS: 123522-75-8
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: FSNORQZDVBPBNW-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-methyl 3-(6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)propanoate 在 偶氮二异丁腈 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 重铬酸吡啶 、 正丁基锂 、 双氧水 、 三正丁基氢锡 、 对甲苯磺酸 、 氟化氢吡啶 、 sodium hydrogensulfite 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 吡啶 、 六甲基磷酰三胺 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+)-Cassiol
  参考文献：
  名称：

  First total synthesis of (+)-cassiol. A potent antiulcerogenic compound

  摘要：

  DOI：

  10.1016/s0040-4039(01)80292-6
• 作为产物：
  描述：

  3-{(R)-1-Methyl-2-[(E)-(S)-1-phenyl-ethylimino]-cyclohexyl}-propionic acid methyl ester 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 (R)-methyl 3-(6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)propanoate
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Riccardiphenols A and B, Isolated from the Liverwort Riccardia crassa

  摘要：

  The title compounds were synthesized as optically active forms using chiral Michael addition of the imine, prepared from 2-methylcyclohexanone and (S)-(-)-phenylethylamine, to methyl propiolate. The etherification of the intermediate triol was accomplished by TsOH-catalyzed cyclization. The absolute configurations of the natural products, riccardiphenols A and B, were established as 1 and 2, respectively.

  DOI：

  10.1021/jo952253u

文献信息

• Gold(III)-Catalyzed Enynamine–Cyclopentadiene Cycloisomerization with Chirality Transfer: An Experimental and Theoretical Study Indicating Involvement of Dual Au(III) Push–Pull Assisted <i>cis</i>–<i>trans</i> Isomerism
  作者：Tom Wirtanen、Mikko Muuronen、Michele Melchionna、Michael Patzschke、Juho Helaja

  DOI：10.1021/jo501905q

  日期：2014.11.7

  been established from chiral enynamines by achiral Au(III) catalysis. On the basis of experimental and theoretical data, the proposed mechanistic pathway from enynamines to Cps occurs via a Au(III) ene cis–trans isomerization step. Computational studies at DFT and NEVPT2 levels advocate that the cis–trans isomerization step proceeds via a dual Au(III) push–pull assisted intermediate with a low computed

  已通过非手性Au（III）催化从手性烯胺建立了一种合成方法，用于合成不对称环稠合的环戊二烯（Cps），该化合物在环结处具有手性碳。根据实验和理论数据，拟议的从烯胺到Cps的机理途径是通过Au（III）烯顺式-反式异构化步骤发生的。在DFT和NEVPT2水平的计算研究认为，顺式-反式异构化步骤是通过双Au（III）推挽辅助中间体进行的，其旋转势垒较低。手性传递通过具有烯丙基特征的螺旋形过渡态发生。催化的范围包括在空间上庞大的烯胺，包括萜烯天然产物。
• Structure–activity relationships of the truncated norzoanthamines exhibiting collagen protection toward anti-osteoporotic activity
  作者：Hironori Inoue、Kazuho Tokita、Seketsu Fukuzawa、Kazuo Tachibana

  DOI：10.1016/j.bmc.2014.04.040

  日期：2014.7

  The marine alkaloid norzoanthamine is a candidate drug for osteoporosis treatment. Due to its structural complexity, simplified analogues possessing similar biological activities are needed for further research. Recently, we found that the bisaminal unit, representing two-thirds of the original structure, is a bioactive equivalent. We synthesized three kinds of further truncated norzoanthamines and evaluated their collagen protection activities. No analog with collagen protection activity comparable to that of the bisaminal unit was found. Thus, we confirmed the importance of the bisaminal unit for the collagen protection activity. Furthermore, we found that the recognition tolerance of the substrate collagen is relatively large by comparing both enantiomers. (C) 2014 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of the core structure of the protein phosphatase inhibitor dysidiolide
  作者：Dirk Brohm、Herbert Waldmann

  DOI：10.1016/s0040-4039(98)00702-3

  日期：1998.6

  The core structure of the protein phosphatase inhibitor dysidiolide and analogs thereof were built up in high yields and with high diastereomer ratios by Diels-Alder reaction between an appropriate diene and an alpha,beta-unsaturated aldehyde. (C) 1998 Elsevier Science Ltd. All rights reserved.