(R)-1,3,4-trimethylcyclohex-3-ene-1-carbaldehyde | 130881-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (R)-1,3,4-trimethylcyclohex-3-ene-1-carbaldehyde
• 英文别名: (R)-1,3,4-trimethyl-cyclohex-3-enecarbaldehyde；(1R)-1,3,4-trimethylcyclohex-3-ene-1-carbaldehyde
• CAS: 130881-20-8
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: HPPUQZZCHCEJEW-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,4R)-pentanediol 、 (R)-1,3,4-trimethylcyclohex-3-ene-1-carbaldehyde 在 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 苯 为溶剂， 生成 (4R,6R)-4,6-Dimethyl-2-((R)-1,3,4-trimethyl-cyclohex-3-enyl)-[1,3]dioxane
  参考文献：
  名称：

  Chiral (acyloxy)borane (CAB): a powerful and practical catalyst for asymmetric Diels-Alder reactions

  摘要：

  DOI：

  10.1021/jo00268a001
• 作为产物：
  描述：

  2-甲基丙烯醛 、 2,3-二甲基-1,3-丁二烯 在 硼烷四氢呋喃络合物 、 monoacylated (2R,3R)-tartaric acid (1a) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 以61%的产率得到(R)-1,3,4-trimethylcyclohex-3-ene-1-carbaldehyde
  参考文献：
  名称：

  Chiral (acyloxy)borane (CAB): a powerful and practical catalyst for asymmetric Diels-Alder reactions

  摘要：

  DOI：

  10.1021/jo00268a001

文献信息

• Chiral Anion Directed Asymmetric Carbocation-Catalyzed Diels-Alder Reactions
  作者：Shengjun Ni、Veluru Ramesh Naidu、Johan Franzén

  DOI：10.1002/ejoc.201501621

  日期：2016.3

  carbocation has re-emerged as a highly efficient Lewis acid catalyst for a variety of organic transformations. However, the goal of asymmetric carbocation catalysis has so far been out of reach mainly as a result of difficulties associated with the preparation of stable chiral carbocations. Here, we describe developments towards asymmetric carbocation catalysis based on the concept of chiral-anion-directed

  近年来，碳正离子重新成为各种有机转化的高效路易斯酸催化剂。然而，迄今为止，不对称碳正离子催化的目标仍然遥不可及，主要是由于与制备稳定的手性碳正离子相关的困难。在这里，我们描述了基于手性阴离子导向催化概念的不对称碳阳离子催化的发展。手性三苯甲基鎓盐可以通过将三苯甲基氯衍生物与手性膦酸盐、磷酰胺、双（磺酰基）酰胺和双（硫酰基）酰胺银盐或钠盐混合而方便地原位制备。结果表明，双（硫基）酰胺/三苯甲基鎓离子盐以高达 53% 的对映体过量催化 Diels-Alder 反应。
• Enantioselective catalysts based on the chiral fragment (η5-C5Me5)Ir(Prophos) for Diels–Alder reactions
  作者：Daniel Carmona、Fernando Viguri、Ainara Asenjo、Fernando J. Lahoz、Pilar García-Orduña、Luis A. Oro

  DOI：10.1016/j.molcata.2014.01.021

  日期：2014.4

  The aqua complex (S-Ir,R-C)-[(eta(5)-C5Me5)Ir(Prophos)(H2O)][SbF6](2) [Prophos = (R)-propane-1,2-diyl-bis(diphenylphosphane)] is an active precursor for the asymmetric Diels-Alder reaction of acyclic enals with cyclopentadiene, 2,3-dimethylbutadiene and isoprene. Enantioselectivities up to 78% ee are achieved. The intermediate Lewis acid-dienophile complex (S-Ir,R-C)-[(eta(5)-C5Me5)Ir(Prophos)(ethyl acrolein)][SbF6](2) has been isolated and completely characterized, including the X-ray crystal structure determination. Structural parameters indicate that the disposition of the coordinated dienophile is controlled by CH/pi attractive interactions established between a phenyl group of the Prophos ligand and the aldehyde proton of the coordinated enal. Proton NMR data indicate that these interactions are maintained in solution. From diffractometric and spectroscopic data, the origin of the enantioselectivity is discussed. (C) 2014 Elsevier B.V. All rights reserved.
• Catalytic Enantioselective Diels−Alder Reaction in Ionic Liquid via a Recyclable Chiral In(III) Complex
  作者：Fan Fu、Yong-Chua Teo、Teck-Peng Loh

  DOI：10.1021/ol062481i

  日期：2006.12.1

  A recyclable, air-and moisture- stable chiral indium complex in [hmim][ PF6-] ionic liquid has been developed. The cycloaddition of a variety of cyclic and open- chained dienes to 2-methacrolein and 2- bromoacrolein resulted in good yields and excellent enantioselectivities ( up to 98% ee). Moreover, the chiral In( III) complex can be reused for seven successive cycles with comparable enantioselectivities and yields without loss of catalytic activity.
• Chiral (acyloxy)borane (CAB): a powerful and practical catalyst for asymmetric Diels-Alder reactions
  作者：Kyoji Furuta、Sadahiro Shimizu、Yoshikazu Miwa、Hisashi Yamamoto

  DOI：10.1021/jo00268a001

  日期：1989.3