(R)-2-benzyloxyhex-5-enal | 147973-69-1

• 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: (R)-2-benzyloxyhex-5-enal
• 英文别名: (2R)-2-phenylmethoxyhex-5-enal
• CAS: 147973-69-1
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: QGERCBKSKXOVDF-CYBMUJFWSA-N

物化性质

• 沸点：
  285.7±35.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-benzyloxyhex-5-enal 在 sodium hydride 、 二异丁基氢化铝 作用下， 生成 S-methyl O-(4R,2E)-4-benzyloxyocta-2,7-dien-1-yl dithiocarbonate
  参考文献：
  名称：

  Stereoselective synthesis of aliphatic 1,5,9,13-polyols using (δ-alkoxyallyl)stannanes

  摘要：

  Treatment of aliphatic aldehydes with the allyltin trichloride generated from the 4-benzyloxyocta-2,7-dienylstannane 18 and tin(IV)chloride provides stereoselective access to polyhydroxylated compounds with the hydroxyl groups at positions 1,5,9,13- etc. along the aliphatic chain.

  DOI：

  10.1016/0040-4039(93)85037-w
• 作为产物：
  描述：

  (R)-5-己烯-1,2-二醇 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 生成 (R)-2-benzyloxyhex-5-enal
  参考文献：
  名称：

  Stereoselective synthesis of aliphatic 1,5,9,13-polyols using (δ-alkoxyallyl)stannanes

  摘要：

  Treatment of aliphatic aldehydes with the allyltin trichloride generated from the 4-benzyloxyocta-2,7-dienylstannane 18 and tin(IV)chloride provides stereoselective access to polyhydroxylated compounds with the hydroxyl groups at positions 1,5,9,13- etc. along the aliphatic chain.

  DOI：

  10.1016/0040-4039(93)85037-w

文献信息

• A new access to enantiopure β-hydroxylated piperidines from N-Boc-2-acyloxazolidines. Application to the synthesis of (−)-desoxoprosopinine and (+)-pseudoconhydrine
  作者：Claude Agami、François Couty、Hubert Lam、Hélène Mathieu

  DOI：10.1016/s0040-4020(98)00508-0

  日期：1998.7

  The synthesis of (−)-desoxoprosopinine and (+)-pseudoconhydrine were achieved from a common oxazolidine precursor. The three stereocenters present in (−)-desoxoprosopinine as well as the two stereocenters of (+)-pseudoconhydrine were created in highly stereoselective ways. The stereoselectivity observed during the reduction of the ketone moiety in the starting oxazolidine was dependent on the occurrence

  从一种常见的恶唑烷前体中可以合成（-）-去氧oprosopinopine和（+）-假conconhydrine。（-）-去氧胸苷的存在的三个立体中心以及（+）-伪conhydrine的两个立体中心是通过高度立体选择性的方式创建的。在起始恶唑烷酮的酮部分还原过程中观察到的立体选择性取决于螯合中间体的存在。其他立体中心是由中间亚胺离子的立体选择性还原或烷基化引起的。
• Synthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective­ Oxypalladation
  作者：Hidefumi Makabe、Yuji Kurogome、Yasunao Hattori

  DOI：10.1055/s-0035-1561114

  日期：——

  Abstract Stereoselective synthesis of decytospolide A and B and their C-3 epimers, which have a 2,6-cis-tetrahydropyran ring, has been achieved in high stereoselectivity and yield. The oxypalladation of single diastereomers of 6-(benzyloxy)-7-hydroxydodec-2-enyl 2-naphthoates was optimized to give products with a 2,6-cis-tetrahydropyran ring with high diastereoselectivity and yield. Stereoselective synthesis

  摘要 具有2,6-顺式-四氢吡喃环的去胞嘧啶A和B及其C-3差向异构体的立体选择性合成已经以高立体选择性和高产率实现。优化了6-（苄氧基）-7-羟基十二烷基-2-苯基-2-萘甲酸单非对映异构体的羟palpalation，得到具有高非对映选择性和收率的带有2,6-顺-四氢吡喃环的产物。 具有2,6-顺式-四氢吡喃环的去胞嘧啶A和B及其C-3差向异构体的立体选择性合成已经以高立体选择性和高产率实现。优化了6-（苄氧基）-7-羟基十二烷基-2-苯基-2-萘甲酸单非对映异构体的羟palpalation，得到具有高非对映选择性和收率的带有2,6-顺-四氢吡喃环的产物。
• Applications of remote stereocontrol using allylstannanes: an approach to the stereoselective synthesis of aliphatic polyols
  作者：Alan H. McNeill、Eric J. Thomas

  DOI：10.1016/j.tet.2010.10.045

  日期：2011.1

  7-dienyl(tributyl)stannane was transmetalated by tin(IV) chloride to generate an allyltin trichloride, which reacted with aldehydes to give (3Z)-1,5-syn-5-benzyloxynona-3,8-dien-1-ols with useful 1,5-stereocontrol. O-Benzylation, hydroboration and oxidation of the terminal double-bond of the product from 2-methylpropanal gave (5R,9S,6Z)-5,9-dibenzyloxy-10-methylundec-6-enal. Further reactions with 4

  （4 R，2 E）-4-苄氧基-辛基-2,7-二烯基（三丁基）锡烷经氯化锡（IV）进行金属转移生成烯丙基三氯化物，该三氯化烯丙基锡与醛反应生成（3 Z）-1，具有有用的1,5-立体控制的5- syn -5-苄氧基壬娜3,8-二烯-1-醇。来自2-甲基丙醛的产物的末端双键的O-苄基化，硼氢化和氧化得到（5 R，9S，6 Z）-5,9-二苄氧基-10-甲基十一烷基-6-烯醛。与4-烷氧基烷-2-烯基锡烷的进一步反应在有用的1,5-立体控制下进行，得到带有羟基或苄氧基取代基的立体选择性地排列在沿链的远端位置的开链产物。
• Formal and total syntheses of herbarumin I and II, respectively from (R)-2,3-cyclohexylideneglyceraldehyde
  作者：Dibakar Goswami、Angshuman Chattopadhyay

  DOI：10.1016/j.tetasy.2012.05.011

  日期：2012.5

  for the formal synthesis of herbarumin I A. Condensation of 7 with 10, another intermediate obtained from 1 afforded 11. The RCM reaction of 11 in the presence of Grubbs second generation catalyst Ru II and global debenzylation of the product in the presence of TiCl4 furnished B. The efficacy of the entire route was due to its operational simplicity, the easy accessibility of 1, all of the reactions

  乙烯基格氏试剂加成到2，通过（的硝基醛醇反应得到的[R）-2,3- cyclohexylideneglyceraldehyde 1，得到3具有绝对立体选择性。将其转化为7，一种已知的中间体，用于形式上的植物素蛋白I A的正式合成。7与10的缩合反应，从1中获得的另一种中间体得到11。在Grubbs第二代催化剂Ru II存在下11的RCM反应和在TiCl 4存在下产物的整体脱苄基作用提供了B。整个路线的有效性归因于其操作简便性，1的易获得性，所有反应都是廉价的以及涉及的不对称C–C键形成反应的高立体选择性以及RCM反应的E选择性。
• Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2005.10.035

  日期：2005.12

  Enantioselective synthesis of alpha-hydroxy aldehydes with an alkene tether was accomplished front L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin. (c) 2005 Elsevier Ltd. All rights reserved.