ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)butanoate | 194470-85-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)butanoate
• 英文别名: ethyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]butyrate；Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]butyrate；Butanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, ethyl ester；ethyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]butanoate
• CAS: 194470-85-4
• 化学式: C₁₀H₁₅F₆O₅P
• 分子量: 360.19
• InChiKey: LCMGMWSLXHIDMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R)-4-((tert-butyldiphenylsilyl)oxy)-2-methylbutanal 、 ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)butanoate 生成
  参考文献：
  名称：

  使用SAMP / RAMP alkyl烷基化方法进行（-）-卡利他汀A的不对称全合成。

  摘要：

  [结构：见正文]已实现（-）-卡利他汀A的不对称全合成。生成立体异构中心的关键步骤依赖于利用SAMP / RAMP alkyl烷基化方法以及3,5-二氧代羧酸酯酶促对映选择性还原的醛或酮的不对称α-烷基化。为了构建烯烃部分，采用了高度选择性的Wittig或Horner-Wadsworth-Emmons反应。

  DOI：

  10.1021/ol0256116
• 作为产物：
  描述：

  2-膦酰丁酸三乙脂 在 五氯化磷 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)butanoate
  参考文献：
  名称：

  有力的抗肿瘤聚酮化合物（-）-Callystatin A †的全合成

  摘要：

  描述了高效抗肿瘤聚酮化合物（-）-卡利他汀A的高度收敛和高效的全合成。合成需要从N-丙酰基恶唑烷酮23开始的19个步骤，并以3.5％的总产率产生所需的产物。

  DOI：

  10.1021/jo050352u

文献信息

• Absolute stereostructure of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata
  作者：Nobutoshi Murakami、Weiqi Wang、Masashi Aoki、Yasuhiro Tsutsui、Kouichi Higuchi、Shunji Aoki、Motomasa Kobayashi

  DOI：10.1016/s0040-4039(97)01194-5

  日期：1997.8

  The unidentified configurations at C5 and C10 in callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, were determined to be R,R by comparing the circular dichroism spectrum of 1 with those of two model compounds 2 and 3. Compounds 2 and 3 were synthesized by using E-selective Wittig olefination at the C6C7 position as a key reaction.

  在C中的未识别的配置5和C 10在callystatin A（1），从海洋海绵一个有效的细胞毒性的聚酮化合物Callyspongia截形，被确定为[R ，- [R通过的圆二色性光谱比较1与两个模型化合物2和3。化合物2和3是通过在C 6 = C 7位置进行E选择性Wittig烯化反应作为关键反应合成的。
• Participation of the conjugated diene part for potent cytotoxicity of callystatin A, a spongean polyketide
  作者：Nobutoshi Murakami、Masanori Sugimoto、Tatsuo Nakajima、Motoyuki Kawanishi、Yasuhiro Tsutsui、Motomasa Kobayashi

  DOI：10.1016/s0968-0896(00)00199-1

  日期：2000.11

  5-epi, 10-epi, 8-Deethyl, and 10-demethyl analogues of callystatin A, a potent cytotoxic spongean polyketide, were synthesized to elucidate structure-requirement for cytotoxic potency. Inversion of the asymmetric center at C-10 in callystatin A minimally affected the activity, while lack of the 10-methyl group in callystatin A decreased cytotoxicity. In addition, the C-5 epimer and the 8-deethyl analogue of callystatin A showed weaker cytotoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe
  作者：Katja Stritzke、Stefan Schulz、Ritsuo Nishida

  DOI：10.1002/1099-0690(200211)2002:22<3884::aid-ejoc3884>3.0.co;2-4

  日期：2002.11

  Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the beta-lactones 1a and 1b is based on a controlled C-C coupling by a Horner-Wadsworth-Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the delta-lactone 3b uses an enantioselective hydrogenation of a dioxoalkanoate precursor. The absolute configurations of the natural lactones 1a, 1b and 3b were determined by gas chromatography on a chiral stationary phase. Both 1a and 1b are of (S,S) configuration, suggesting their biosynthetic origin from (-)-viridifloric acid (7a) or (-)norviridifloric acid (7b), respectively. In contrast, natural 3b is a mixture of all enantiomers, in which the (5S,7S) enantiomer dominates.
• MICHAELIS-BECKER SYNTHESIS OF<i>bis</i>(2,2,2-TRIFLUOROETHYL)PHOSPHONO ESTERS
  作者：Gregory M. Ciszewski、John A. Jackson

  DOI：10.1080/00304949909355724

  日期：1999.4
• Total Synthesis of (−)-Callystatin A
  作者：James A. Marshall、Matthew P. Bourbeau

  DOI：10.1021/jo016025d

  日期：2002.5.1

  A total synthesis of the cytotoxic polyketide marine natural product callystatin A is described. The route features chiral allenylmetal additions to construct the polypropionate C15-22 segment and an sp(2)-sp(3) Suzuki coupling to join the C1-C11 and C12-C22 subunits.