(2Z)-4-(benzyloxy)-2-methylbut-2-en-1-ol | 115827-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z)-4-(benzyloxy)-2-methylbut-2-en-1-ol
• 英文别名: (Z)-4-(benzyloxy)-2-methyl-2-buten-1-ol；(Z)-2-methyl-4-phenylmethoxybut-2-en-1-ol
• CAS: 115827-26-4
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: ZBNQXXPQZJJMIB-XFFZJAGNSA-N

物化性质

• 沸点：
  310.3±30.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2Z)-4-(benzyloxy)-2-methylbut-2-en-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 邻苯二甲酸二甲酯 、 碳酸氢钠 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Tetrasubstituted Pyrrolidines via a Tandem Aza-Payne/Hydroamination Reaction

  摘要：

  A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination.

  DOI：

  10.1021/ja068077w
• 作为产物：
  描述：

  异戊烯醇 在 叔丁基过氧化氢 、 sodium tetrahydroborate 、 selenium(IV) oxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 36.0h， 生成 (2Z)-4-(benzyloxy)-2-methylbut-2-en-1-ol
  参考文献：
  名称：

  Tetrasubstituted Pyrrolidines via a Tandem Aza-Payne/Hydroamination Reaction

  摘要：

  A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination.

  DOI：

  10.1021/ja068077w

文献信息

• Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement
  作者：G. William Daub、James P. Edwards、Carol R. Okada、Jana Westran Allen、Claudia Tata Maxey、Matthew S. Wells、Alexandra S. Goldstein、Michael J. Dibley、Clarence J. Wang、Daniel P. Ostercamp、Steven Chung、Paula Shanklin Cunningham、Martin A. Berliner

  DOI：10.1021/jo9614250

  日期：1997.4.1

  The ortho ester Claisen rearrangement of trisubstituted allylic alcohols exhibits significant levels of diastereoselection. In E allylic alcohols, a 1,3-diaxial interaction develops in the chairlike transition state leading to the anti isomer, rendering the reaction syn selective by a factor of 3-5 to 1. In Z allylic alcohols, the 1,3-diaxial interaction develops in the transition state leading to

  三取代的烯丙基醇的原酸酯克莱森重排表现出显着水平的非对映选择性。在E烯丙基醇中，在椅子状过渡状态下会形成1,3-二轴相互作用，从而导致反异构体，使反应的Syn选择性达到3-5：1。在Z烯丙基醇中，1,3-二轴相互作用相互作用以过渡状态发展，导致顺式异构体，产生6-15对1的反式：顺式选择性。顺式异构体的相对立体化学是通过霉菌毒素葡萄孢菌素的合成独立确定的。
• Highly anti selective SN2′ additions of LiMe2Cu to chiral acyclic vinyloxiranes
  作者：James A. Marshall、Joseph D. Trometer、Bruce E. Blough、Thomas D. Crute

  DOI：10.1016/s0040-4039(00)82480-6

  日期：1988.1

  Additions of LiMe2Cu to the trans and cis-Z vinyloxiranes 8 and 10 proceed with virtually 100% anti diastereoface selectivity to afford the syn-Z diol 12 and the anti-E diol 13 as the major products.

  石灰添加2与Cu的反式与顺式-Z vinyloxiranes 8和10，几乎100％的反diastereoface选择性进行，得到顺式-Z二醇12和抗E二醇13作为主要产物。
• Stereoselective synthesis of orthogonally protected 2,3-disubstituted morpholines using a base-catalysed cascade reaction
  作者：Frederic J. Marlin

  DOI：10.1016/j.tetlet.2017.06.077

  日期：2017.8

  The stereoselective synthesis of differentially protected [3-(hydroxymethyl)morpholin-2-yl]methanols is described, starting from chiral epoxides. The key step involves a one-pot oxazolidinone formation via intramolecular epoxide opening and concomitant cyclisation to form the morpholine ring. Selective deprotection reveals the free hydroxymethyl group at either the 2- or 3-position of the morpholine

  从手性环氧化物开始，描述了立体保护的[3-（羟甲基）吗啉-2-基]甲醇的立体选择性合成。关键步骤涉及通过分子内环氧化物开放并伴随环化形成吗啉环，形成一锅的恶唑烷酮。选择性脱保护揭示了吗啉2位或3位的游离羟甲基。
• Total synthesis of (+)-conagenin
  作者：Tushar Kanti Chakraborty、Gangarajula Sudhakar

  DOI：10.1016/j.tetlet.2006.06.087

  日期：2006.8

  The total synthesis of the immunomodulator, (+)-conagenin was achieved using, as a key step, a method developed by us for the synthesis of 2-methyl-1,3-diols via Ti(III)-mediated diastereo- and regioselective opening of trisubstituted 2,3-epoxy alcohols, to carry out the stereoselective construction of its pentanoic acid segment.

  免疫调节剂（+）-conagenin的总合成是关键步骤，它是我们开发的通过Ti（III）介导的非对映选择性和区域选择性合成2-甲基-1,3-二醇的方法作为关键步骤打开三取代的2，3-环氧醇，以进行其戊酸链段的立体选择性构建。
• Stereochemistry of SN2' additions to acyclic vinyloxiranes
  作者：James A. Marshall、Joseph D. Trometer、Bruce E. Blough、Thomas D. Crute

  DOI：10.1021/jo00253a020

  日期：1988.9