5,5-diethoxy-pent-1-yn-3-ol | 80982-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-diethoxy-pent-1-yn-3-ol
• 英文别名: 3-Hydroxy-4-pentynal diethyl acetal；5,5-diethoxypent-1-yn-3-ol
• CAS: 80982-35-0
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: SUVLKQWRAPHVAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• 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：

  5,5-diethoxy-pent-1-yn-3-ol 在 sodium hydroxide 、 无水二甲氨基乙醇 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 苯 为溶剂， 反应 18.33h， 生成 2-((S)-2-Benzyloxy-but-3-ynyl)-5,5-dimethyl-[1,3]dioxane
  参考文献：
  名称：

  Total synthesis of maytansinoids. Approach to 4,6-bisdemethylmaytansine and 4-demethylmaytansine

  摘要：

  A convergent strategy was elaborated to synthesize maytansine 1 and maytansinoids modified on the carbon skeleton, especially 4-demethylmaytansine 2, 6-demethylmaytansine 3, 4,6-bisdemethylmaytansine 4. In this paper, the feasibility of the project was verified by the preparation of key intermediates for the synthesis of 4, 6-bisdemethylmaytansine and 6-demethylmaytansine. The C-1-N open chain compound 18 in the 4,6-bisdemethyl series was obtained.

  DOI：

  10.1016/s0040-4020(01)88513-6
• 作为产物：
  描述：

  丙烯醛缩二乙醇 在 sodium hydroxide 、 重铬酸吡啶 、 正丁基锂 、 dimethyl sulfide borane 、 3 A molecular sieve 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 5,5-diethoxy-pent-1-yn-3-ol
  参考文献：
  名称：

  Total synthesis of maytansinoids. Approach to 4,6-bisdemethylmaytansine and 4-demethylmaytansine

  摘要：

  A convergent strategy was elaborated to synthesize maytansine 1 and maytansinoids modified on the carbon skeleton, especially 4-demethylmaytansine 2, 6-demethylmaytansine 3, 4,6-bisdemethylmaytansine 4. In this paper, the feasibility of the project was verified by the preparation of key intermediates for the synthesis of 4, 6-bisdemethylmaytansine and 6-demethylmaytansine. The C-1-N open chain compound 18 in the 4,6-bisdemethyl series was obtained.

  DOI：

  10.1016/s0040-4020(01)88513-6

文献信息

• Chemistry of acetals
  作者：L. A. Yanovskaya、V. F. Kucherov、B. G. Kovalev

  DOI：10.1007/bf00904764

  日期：1962.4
• Raifel'd, Yu. E.; Zil'berg, L. L.; Arshava, B. M., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 11, p. 2036 - 2039
  作者：Raifel'd, Yu. E.、Zil'berg, L. L.、Arshava, B. M.、Makin, S. M.

  DOI：——

  日期：——
• Chemistry of polyenic and polyacetylenic compounds communication 8. Methods of synthesizing polyenic dicarboxylic acids having even numbers of double bonds and also polyenynic dicarboxylic acids
  作者：B. G. Kovalev、L. A. Yanovskaya、V. F. Kucherov、G. A. Kogan

  DOI：10.1007/bf00846962

  日期：1963.1
• RAJFELD, YU. E.;ZILBERG, L. L.;ARSHAVA, B. M.;MAKIN, S. M., ZH. ORGAN. XIMII, 1981, 17, N 11, 2281-2284
  作者：RAJFELD, YU. E.、ZILBERG, L. L.、ARSHAVA, B. M.、MAKIN, S. M.

  DOI：——

  日期：——
• Total synthesis of maytansinoids. Approach to 4,6-bisdemethylmaytansine and 4-demethylmaytansine
  作者：Michel Bénéchie、Bernard Delpech、Qui Khuong-Huu、Françoise Khuong-Huu

  DOI：10.1016/s0040-4020(01)88513-6

  日期：1992.1

  A convergent strategy was elaborated to synthesize maytansine 1 and maytansinoids modified on the carbon skeleton, especially 4-demethylmaytansine 2, 6-demethylmaytansine 3, 4,6-bisdemethylmaytansine 4. In this paper, the feasibility of the project was verified by the preparation of key intermediates for the synthesis of 4, 6-bisdemethylmaytansine and 6-demethylmaytansine. The C-1-N open chain compound 18 in the 4,6-bisdemethyl series was obtained.