rac-2-hydroxyhex-5-enenitrile | 177793-91-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: rac-2-hydroxyhex-5-enenitrile
• 英文别名: 2-Hydroxy-5-hexenenitrile；2-hydroxyhex-5-enenitrile
• CAS: 177793-91-8
• 化学式: C₆H₉NO
• 分子量: 111.144
• InChiKey: XABRSSBCRXNZEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-2-hydroxyhex-5-enenitrile 在 2,6-二甲基吡啶 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 rac-2-[dimethyl(phenyl)silyl]hex-5-enenitrile
  参考文献：
  名称：

  构型反转下铜催化α-三氟乙腈和酯被硅亲核试剂取代

  摘要：

  铜催化的α-三氟乙腈和酯与硅亲核试剂的亲核取代反应可以立体定向生成高度对映体富集的α-甲硅烷基化的羧基化合物。α-甲硅烷基化腈的对映选择性合成是前所未有的。催化体系表现出良好的官能团耐受性。取代的立体化学过程显示为反转构型。新的反应是对催化C（sp 3）-Si交叉偶联方法数量仍然有限的补充。

  DOI：

  10.1021/acs.orglett.7b03279
• 作为产物：
  描述：

  4-戊烯醛 以 乙醇 为溶剂， 反应 3.0h， 以72%的产率得到rac-2-hydroxyhex-5-enenitrile
  参考文献：
  名称：

  Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis

  摘要：

  Routes to the four regioisomeric 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols have been developed, and in the racemic series, mercury(II)-mediated reactions of appropriate dienone, hydroxy enone, dienedione, and hydroxy dienone systems have been exploited. Most of the epimeric pairs of alcohols (i.e. axial or equatorial) in the E,E, E,Z, or Z,E spiroacetal ring systems have been characterized by detailed H-1, C-13, and correlated NMR spectroscopy and mass spectrometry. Key enantiomers of these alcohols have been obtained by elaborating chiral starting materials such as D-mannitol, L-arabinose, poly(hydroxybutyrate), and in the case of the 5-hydroxy derivative, mandelonitrile lyase mediated formation of a key chiral cyanohydrin was employed. Most of the alcohols, as their trifluoroacetates, are resolved (into enantiomers) on a Lipodex A GC column, thus facilitating their identification from natural sources. In this way, the absolute configurations of a number of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols present in the rectal gland secretion of Bactrocera cucumis (cucumber fly) have been determined.

  DOI：

  10.1021/jo00038a027

文献信息

• Herbicidal cyano-tetrahydrofuranylmethyl ether and
  申请人：Shell Oil Company

  公开号：US04439225A1

  公开（公告）日：1984-03-27

  Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or alkyl; n is 0 or 1 and R is an unsaturated moiety, are useful as herbicides and plant growth regulators.

  公式为##STR1##的化合物，其中R.sup.1和R.sup.2为H或烷基；n为0或1，R为不饱和基团，可用作除草剂和植物生长调节剂。
• 2-Cyano-tetrahydrofuran-5-methanols
  申请人：Shell Oil Company

  公开号：US04493936A1

  公开（公告）日：1985-01-15

  Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or alkyl; n is 0 or 1 and R is an unsaturated moiety, are useful as herbicides and plant growth regulators.

  式为##STR1##的化合物，其中R.sup.1和R.sup.2为H或烷基；n为0或1，R为不饱和基团，可用作除草剂和植物生长调节剂。
• Method of producing optically active alpha-hydroxy acid or alpha-hydroxyamide
  申请人：MITSUBISHI RAYON CO., LTD.

  公开号：EP0711836B1

  公开（公告）日：2000-02-02
• US4439225A
  申请人：——

  公开号：US4439225A

  公开（公告）日：1984-03-27
• US4493936A
  申请人：——

  公开号：US4493936A

  公开（公告）日：1985-01-15