(2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)methanol | 145315-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)methanol
• 英文别名: (2R,3S)-3-allyloxy-2-hydroxymethyl-3,4,5,6-tetrahydro-2H-pyran；[(2R,3S)-3-prop-2-enoxyoxan-2-yl]methanol
• CAS: 145315-46-4
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: UVSTVUKQNZSRPB-DTWKUNHWSA-N

物化性质

• 沸点：
  269.7±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)methanol 在 bis(tricyclohexylphosphine)benzylidine ruthenium(IV) di 、 盐酸 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (Z)-(4aS,23aR)-16-methylene-2,3,4,4a,6,9,12,13,16,17,20,21,23,23a-tetradecahydro-11H,15H,19H-1,5,10,14,18,22-hexaoxabenzocycloheneicosene
  参考文献：
  名称：

  Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles

  摘要：

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.

  DOI：

  10.1021/jo9901438
• 作为产物：
  描述：

  (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)tetrahydropyran-3-ol 在 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)methanol
  参考文献：
  名称：

  Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles

  摘要：

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.

  DOI：

  10.1021/jo9901438

文献信息

• Kadota, Isao; Kobayashi, Katsumi; Okano, Hiroshi, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 615 - 623
  作者：Kadota, Isao、Kobayashi, Katsumi、Okano, Hiroshi、Asao, Naoki、Yamamoto, Yoshinori

  DOI：——

  日期：——
• Asymmetric synthesis of syn 1,2-diols via the reaction of aldehydes with chiral .gamma.-(tetrahydropyranyloxy)allylstannanes
  作者：Yoshinori Yamamoto、Katsumi Kobayashi、Hiroshi Okano、Isao Kadota

  DOI：10.1021/jo00052a002

  日期：1992.12

  Asymmetric synthesis of syn 1,2-diols 3 has been accomplished via the reaction of the chiral gamma-alkoxy-substituted allylstannane 1 with aldehydes in the presence of AlCl3 or AlCl3.OEt2, followed by a five-step operation to remove the chiral auxiliary.
• Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles
  作者：Mercedes Delgado、Julio D. Martín

  DOI：10.1021/jo9901438

  日期：1999.6.1

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.