cis-2-methyl-2,3-dihydro-4H-pyran-4-yl acetate | 69734-22-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-2-methyl-2,3-dihydro-4H-pyran-4-yl acetate
• 英文别名: 3-O-acetyl-4,6-deoxy-(+/-)-glucal；[(2R,4S)-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate
• CAS: 69734-22-1；130010-13-8；138512-08-0
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: DOHJFQHYGJPEFE-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11,12-dihydroindolo[2,3-a]carbazole 、 cis-2-methyl-2,3-dihydro-4H-pyran-4-yl acetate 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到
  参考文献：
  名称：

  Indolocarbazoles. 4. Synthetic studies towards staurosporine and tjipanazoles: Reactions of indolocarbazole with glycals

  摘要：

  In an attempt to construct the unique N,N'-bidentate glycosyl linkage found in the Staurosporine 1 class of natural products, the first example of an acid catalyzed 2,6-condensation of an activated pyran with indolocarbazole 4 is reported. In pursuit of the real system, a variety of glycals were reacted with indolocarbazole 4. Formation of novel unexpected products (B/C) with 13-connections along with the expected product (A) and its' synthetic transformation to a potentially useful intermediate 24 are detailed.

  DOI：

  10.1016/s0040-4039(00)76813-4
• 作为产物：
  描述：

  2-methyl-2,3-dihydro-4H-pyran-4-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 cis-2-methyl-2,3-dihydro-4H-pyran-4-yl acetate
  参考文献：
  名称：

  Varelis, Peter; Graham, Alan J.; Johnson, Brian L., Australian Journal of Chemistry, 1994, vol. 47, # 9, p. 1735 - 1740

  摘要：

  DOI：

文献信息

• Enzymatic resolution of racemic glycals: an application of the wong acylation method
  作者：David B. Berkowitz、Samuel J. Danishefsky

  DOI：10.1016/0040-4039(91)80067-g

  日期：1991.9

  Kinetic resolution of racemic, fully synthetic, artificial glycals bearing a free hydroxyl group at C3 was accomplished through the more rapid acylation of the ''D''-antipode with vinyl acetate as acyl donor and Lipase PS-30 from Pseudomonas cepacia as catalyst.
• Varelis, Peter; Graham, Alan J.; Johnson, Brian L., Australian Journal of Chemistry, 1994, vol. 47, # 9, p. 1735 - 1740
  作者：Varelis, Peter、Graham, Alan J.、Johnson, Brian L.、Skelton, Brian W.、White, Allan H.

  DOI：——

  日期：——
• Indolocarbazoles. 4. Synthetic studies towards staurosporine and tjipanazoles: Reactions of indolocarbazole with glycals
  作者：B.B. Shankar、S.W. McCombie

  DOI：10.1016/s0040-4039(00)76813-4

  日期：1994.5

  In an attempt to construct the unique N,N'-bidentate glycosyl linkage found in the Staurosporine 1 class of natural products, the first example of an acid catalyzed 2,6-condensation of an activated pyran with indolocarbazole 4 is reported. In pursuit of the real system, a variety of glycals were reacted with indolocarbazole 4. Formation of novel unexpected products (B/C) with 13-connections along with the expected product (A) and its' synthetic transformation to a potentially useful intermediate 24 are detailed.