(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-1-ol | 186258-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-1-ol
• 英文别名: (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-4-en-1-ol
• CAS: 186258-69-5
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: XJSFRPDSKRKHNP-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-1-ol 在 咪唑 、 sodium hydride 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Ansa Macrolides as Molecular Workbenches: Stereocontrolledsyn Additions toE olefins

  摘要：

  Fixed on an aromatic platform in a conformationally defined way, acyclic (E)-alkenes can be considered gripped on a molecular workbench. The olefinic ansa-macrolides formed in this way are shielded on one face. On epoxidation and dihydroxylation [Eq. (1)] the attack on the double bond takes place diastereoselectively from outside the ring, and the ansa chain can subsequently be cleaved from the workbench by mild hydrogenolysis. Bn=benzyl, NMO=N-methylmorpholin-N-oxide.

  DOI：

  10.1002/(sici)1521-3773(19980619)37:11<1566::aid-anie1566>3.0.co;2-u
• 作为产物：
  描述：

  4-溴-1-丁烯 、 (2R,3S)-3,4-epoxy-1,2-O-isopropylidenebutane-1,2-diol 在 magnesium 作用下， 以 乙醚 为溶剂， 以79 %的产率得到(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-1-ol
  参考文献：
  名称：

  Aigialomycin D 的另一种全合成

  摘要：

  Aigialomycin D 是一种 14 元苯环化大环内酯，采用廉价且常见的起始原料，通过简单、高效和立体选择性的方法合成。主要的 ...

  DOI：

  10.1080/00397911.2024.2358355

文献信息

• Enantioselective synthesis of medium-ring sub-units of brevetoxin A by ring-closing metathesis
  作者：J. Stephen Clark、Jason G. Kettle

  DOI：10.1016/s0040-4039(96)02233-2

  日期：1997.1

  A new strategy for the enantioselective synthesis of eight- and nine-membered cyclic ethers corresponding to sub-units of brevetoxin A has been developed. The strategy involves the use of ring-closing metathesis reactions of allylic ethers to effect ring construction.

  已经开发了一种新的策略，用于对映异构合成短分子毒素A亚基的八元和九元环状醚。该策略涉及使用烯丙基醚的闭环复分解反应以实现环的构建。
• Studies toward the total synthesis of Cytospolide E
  作者：Paresh M. Vadhadiya、Jeetendra K. Rout、C.V. Ramana

  DOI：10.1016/j.tet.2015.10.018

  日期：2015.12

  In this manuscript, we describe various approaches that we have examined towards the total synthesis of Cytospolide E. We initially attempted the RCM approach employing first and second generation Grubbs and Grubbs-Hoyeda catalysts resulting in the exclusive synthesis of the Z-isomer of Cytospolide E. With the Furstner catalyst, the dimerization involving the less hindered olefin was the exclusive event. Alternative approach documented is a successful cross-metathesis leading to a seco-acid with the requisite E-configuration and undesired macrodiolide formation during the attempted Shiina's lactonization. (C) 2015 Elsevier Ltd. All rights reserved.
• Harnessing Glycal-Epoxide Rearrangements: The Generation of the AB, EF, and IJ Rings of Adriatoxin
  作者：Clement Osei Akoto、Jon D. Rainier

  DOI：10.1002/anie.200803791

  日期：2008.10.6
• Allylic C−H Amination for the Preparation of <i>syn</i>-1,3-Amino Alcohol Motifs
  作者：Grant T. Rice、M. Christina White

  DOI：10.1021/ja9054959

  日期：2009.8.26

  A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.
• An Experimental and Theoretical Study of a Bicyclic Acetal Equilibrium
  作者：Andrew P Dominey、Jonathan M Goodman

  DOI：10.1021/ol990669e

  日期：1999.8.1

  [GRAPHICS]The position of equilibrium for competitive acetal formation can be hard to predict. This example, the core of zaragozic acid, is finely balanced, but an experimental investigation has proved that the left-hand isomer is preferred. Molecular mechanics force fields are unable to cope with such systems, because there is competition between five- and six-membered rings. Results from these calculations should not be used to estimate the position of equilibrium in such cases.