R-(+)-2-ethyl-1,4-butanediol | 74650-55-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: R-(+)-2-ethyl-1,4-butanediol
• 英文别名: (2R)-2-ethylbutane-1,4-diol；(2R)-ethylbutane-1,4-diol；2-Ethyl-1,4-butanediol
• CAS: 74650-55-8
• 化学式: C₆H₁₄O₂
• 分子量: 118.176
• InChiKey: CYVMBANVYOZFIG-ZCFIWIBFSA-N

物化性质

• 沸点：
  116 °C(Press: 8 Torr)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  R-(+)-2-ethyl-1,4-butanediol 在 三溴化磷 作用下， 以 吡啶 为溶剂， 以13.2 g的产率得到R-(-)-2-ethyl-1,4-dibromobutane
  参考文献：
  名称：

  Bettoni, Giancarlo; Cellucci, Carla; Berardi, Francesco, Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 603 - 605

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2-Ethylbutannedioic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 R-(+)-2-ethyl-1,4-butanediol
  参考文献：
  名称：

  Bettoni, Giancarlo; Cellucci, Carla; Berardi, Francesco, Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 603 - 605

  摘要：

  DOI：

文献信息

• Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries
  作者：Jing Lin、Wing Hong Chan、Albert W.M. Lee、Wai Yeung Wong

  DOI：10.1016/s0040-4020(99)00872-8

  日期：1999.12

  The use of enantiomerically pure sultams (+)-1 and (−)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α-bromopropanoate or α-bromobutanoate

  完整描述了对映体纯的阿马酚（+）- 1和（-）- 1作为不对称烷基化反应的实际手性助剂。衍生自助剂的N-酰化产物用六甲基二硅叠氮化钠脱质子，然后用烷基卤化物处理，得到具有高非对映选择性的产物。用过量的外消旋α-溴丙酸酯或α-溴丁酸酯处理时，相应的N-酰基sultam的烯酸酯经历高度非对映选择性烷基化，以提供完全绝对控制两个连续手性中心的产物。
• Enantioselective synthesis of (R)- and (S)-2-alkyl-1,4-butanediolsvia enantiomerically pure 3-alkyl-5-(menthyloxy)butyrolactones
  作者：Namkyu Lee、Young-Woo Kim、Kieyoung Chang、Key H. Kim、Sang-Sup Jew、Dae-Kee Kim

  DOI：10.1016/0040-4039(96)00310-3

  日期：1996.4

  A general and practical symthesis of optically pure (R)- and (S)-2-ethyl, 2-propyl and 2-isopropyl-1,4-butanediols, 9a-c, has been accomplished from optically pure 5-(menthyloxy)butenolides in five steps in good yields.

  光学纯的（R）-和（S）-2-乙基，2-丙基和2-异丙基-1,4-丁二醇9a-c的一般和实用合成是由光学纯的5-（薄荷基氧基）完成的分五个步骤生产丁烯内酯，收率高。
• Synthesis and absolute configuration of the insecticidal sesquilignan (+)-HAEDOXAN a in honour of professor G. H. Neil Towers 75th birthday
  作者：Fumito Ishibashi、Eiji Taniguchi

  DOI：10.1016/s0031-9422(98)00270-2

  日期：1998.9

  The insecticidal neolignan, (+)-haedoxan A, was synthesized from (S)-(+)-beta-vinyl-gamma-butyrolactone and (2R,3R)-(+)-6-formyl-7-methoxy-3-methoxymethyl-2-(3,4-methylenedioxyphenyl)-1,4-benzodioxane, and its absolute configuration was unequivocally established as 1S,2R,5R,6S,2"R,3''R. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of 1,3- and 1,3,4-substituted pyrrolidines
  作者：Jing Lin、Wing Hong Chan、Albert W.M Lee、Wai Yeung Wong、Pei Qiang Huang

  DOI：10.1016/s0040-4039(00)00278-1

  日期：2000.4

  Diastereoselective alkylation of N-acylnorbornene sultams 2 afforded a variety of enantiomerically pure products 3a-3e. Reduction with LiAlH4 (LAH) followed by ditosylation furnished chiral 1,4-ditosylates 5a-5e which underwent a cyclization reaction with primary amines to afford chiral 1,3- and 1,3;4-substituted pyrrolidines. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Diastereoselective conjugate addition of Grignard reagents to a homochiral fumaramide derived from Oppolzer’s sultam
  作者：Gary P. Reid、Kieron W. Brear、David J. Robins

  DOI：10.1016/j.tetasy.2003.12.010

  日期：2004.3

  Conjugate addition of Grignard reagents to N,N'-fumaroylbis[(2R)-bornane-10,2-sultam] 1 occurred with moderate to high levels of diastereoselectivity. Diastereomeric excesses were estimated by analysis of the H-1 NMR spectra of the succinamide mixtures and enantiomeric excesses from F-19 NMR spectra of the bis Mosher esters of the diols produced by reductive cleavage of the succinamides. Saponification of the succinamides gave the corresponding (R)-succinic acids with ees up to 92% showing that addition of the Grignard reagents takes place selectively on the re-face of 1. (C) 2003 Elsevier Ltd. All rights reserved.