2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-2-methylpropan-1-ol | 104708-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-2-methylpropan-1-ol
• CAS: 104708-08-9
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: NZQKSLNPUWCEKK-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-2-methylpropan-1-ol 在 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 17.5h， 生成 (2R)-4-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutane-1,2-diol
  参考文献：
  名称：

  Bryostatins: The Asymmetric Synthesis of the C₁-C₉and C₁₇-C₂₇Fragments

  摘要：

  构建了布雷抑酶素（bryostatins）的片段C1-C9 3和C17-C27 4a，采用了对映选择性和高非对映选择性的方式。通过分别以D-泛醇内酯（6）和D-异丁基乳酸酯（23）为手性模板合成这些片段，说明了“四手型”方法的实用性。

  DOI：

  10.1055/s-1994-25589
• 作为产物：
  描述：

  D-(-)-泛酰内酯 在 对甲苯磺酸 lithium aluminium tetrahydride 、 sodium sulfate 作用下， 以 四氢呋喃 为溶剂， 生成 2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-2-methylpropan-1-ol
  参考文献：
  名称：

  Convenient access to two enantiomeric oxirane synthons bearing a quaternary gem-dimethyl carbon center: Synthesis of 3S-(+) and 3R-(−)-2,2-dimethyl-3,4-oxo-1-butanol from R-(−)-pantolactone

  摘要：

  DOI：

  10.1016/s0040-4039(00)84071-x

文献信息

• Syntheses and Biological Evaluation of Irciniastatin A and the C1−C2 Alkyne Analogue
  作者：Tsubasa Watanabe、Takamichi Imaizumi、Takumi Chinen、Yoko Nagumo、Masatoshi Shibuya、Takeo Usui、Naoki Kanoh、Yoshiharu Iwabuchi

  DOI：10.1021/ol1000389

  日期：2010.3.5

  Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.
• Design, synthesis, and evaluation of novel kazusamycin A derivatives as potent antitumor agents
  作者：Ryoichi Ando、Yusaku Amano、Hideo Nakamura、Noriyoshi Arai、Isao Kuwajima

  DOI：10.1016/j.bmcl.2006.03.056

  日期：2006.6

  Novel kazusamycin A derivatives were designed in the viewpoint of decrease of reactivity at the alpha,beta-unsaturated delta-lactone moiety against Michael-type addition. Although 25-30 steps were required for the synthesis of each compound, their syntheses were achieved. Cytotoxicity against HPAC cell line was evaluated, and two of them exhibited comparable potency to kazusamycin A. Hepatic toxicity of these designed compounds was much lower than that of kazusamycin A. (c) 2006 Elsevier Ltd. All rights reserved.
• Honda, Toshio; Satoh, Masayuki; Kobayashi, Yuji, Journal of the Chemical Society. Perkin transactions I, 1992, # 13, p. 1557 - 1558
  作者：Honda, Toshio、Satoh, Masayuki、Kobayashi, Yuji

  DOI：——

  日期：——
• Bryostatins: The Asymmetric Synthesis of the C₁-C₉and C₁₇-C₂₇Fragments
  作者：Jef De Brabander、Maurits Vandewalle

  DOI：10.1055/s-1994-25589

  日期：——

  The construction of the fragments C1-C9 3 and C17-C27, 4a of the bryostatins in a enantioselective and highly diastereoselective fashion is described. The usefulness of the "chiron" approach is illustrated with the synthesis of these fragments from, respectively, D-pantolactone (6) and D-isobutyl lactate (23) as chiral templates.

  构建了布雷抑酶素（bryostatins）的片段C1-C9 3和C17-C27 4a，采用了对映选择性和高非对映选择性的方式。通过分别以D-泛醇内酯（6）和D-异丁基乳酸酯（23）为手性模板合成这些片段，说明了“四手型”方法的实用性。
• Convenient access to two enantiomeric oxirane synthons bearing a quaternary gem-dimethyl carbon center: Synthesis of 3S-(+) and 3R-(−)-2,2-dimethyl-3,4-oxo-1-butanol from R-(−)-pantolactone
  作者：Pierre Lavallée、Réjean Ruel、Louis Grenier、Martine Bissonnette

  DOI：10.1016/s0040-4039(00)84071-x

  日期：1986.1