carboethoxy-iodotriphenylphosphonium methylidene | 26480-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: carboethoxy-iodotriphenylphosphonium methylidene
• 英文别名: ethoxycarbonyliodomethyltriphenylphosphorane；triphenylcarbethoxyiodomethylenephosphorane；(ethoxycarbonyliodomethylidene)triphenylphosphorane；Ethyl-iod-(triphenylphosphoranyliden)-acetat；Ph3P=C(I)CO2Et；Ethyl 2-iodo-2-(triphenylphosphoranylidene)acetate；ethyl 2-iodo-2-(triphenyl-λ5-phosphanylidene)acetate
• CAS: 26480-87-5
• 化学式: C₂₂H₂₀IO₂P
• 分子量: 474.278
• InChiKey: BGTGWSQNAUBYSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  菲醌 、 carboethoxy-iodotriphenylphosphonium methylidene 生成 2-O-ethyl 3-O-methyl phenanthro[9,10-b]furan-2,3-dicarboxylate
  参考文献：
  名称：

  Nicolaides Demetrios N., Litinas Konstantinos E., Lefkaditis DemetriosA.,+, J. Chem. Soc. Perkin Trans. 1, (1994) N 15, S 2107- 2112

  摘要：

  DOI：

文献信息

• Synthesis of the neocarzinostatin chromophore A core diynene structure using an η²-hexacarbonyidicobalt mediated Aldol reaction
  作者：Philip Magnus、Thomas Pitterna

  DOI：10.1039/c39910000541

  日期：——

  The monoketal of cyclopentene-1,3-dione was converted into the η2-Co2(CO)6 neocarzinostatin core 19 in six steps; oxidative decomplexation in the presence of cyclohexa-1,4-diene gave the cycloaromatized adduct 22.

  环戊烯-1,3-二酮的单缩酮转化成η 2 -Co 2（CO）6新制癌菌素核心19在六个步骤; 环己1,4-二烯存在下的氧化分解产生了环芳香化的加合物22。
• Development of Highly Stereoselective Asymmetric 6π-Azaelectrocyclization of Conformationally Flexible Linear 1-Azatrienes. From Determination of Multifunctional Chiral Amines, 7-Alkyl <i>cis</i>-1-Amino-2-indanols, to Application as a New Synthetic Strategy:  Formal Synthesis of 20-Epiuleine
  作者：Katsunori Tanaka、Toyoharu Kobayashi、Hajime Mori、Shigeo Katsumura

  DOI：10.1021/jo049381f

  日期：2004.9.1

  The highly stereoselective asymmetric 6π-azaelectrocyclization was achieved as a general synthetic method based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (−)-7-alkyl-cis-1-amino-2-indanol derivatives which are effective chiral amines. The 7-alkyl-substituted 2-indanol moiety of the cyclized products was efficiently removed by the novel manganese dioxide oxidation under

  根据（E）-3-羰基-2,4,6-三烯基化合物与（-）-7-烷基-顺式-1-的反应，通过常规合成方法实现了高度立体选择性的不对称6π-氮杂电环化是有效的手性胺的氨基-2-茚满醇衍生物。在明显温和的条件下，通过新型的二氧化锰氧化可有效去除环化产物中的7-烷基取代的2-茚满醇部分，并将该方法成功地用于光学活性的20-表柔比林的形式合成中。
• Synthetic studies toward biselides. Part 1: synthesis of the core carbon framework of biselides A, B, and E using Stille coupling
  作者：Yohsuke Satoh、Dai Kawamura、Masashi Yamaura、Yoichi Ikeda、Yumi Ochiai、Ichiro Hayakawa、Hideo Kigoshi

  DOI：10.1016/j.tetlet.2012.01.020

  日期：2012.3

  Biselides A and B are cytotoxic marine polyketides. We have achieved synthesis of the C-1–C-15 segment of biselides A and B by using Stille coupling and regioselective oxidative cleavage as key steps. Furthermore, we constructed the α,β-unsaturated lactone part of biselide E by using a similar strategy.

  Biselides A和B是具有细胞毒性的海洋聚酮化合物。通过使用Stille偶联和区域选择性氧化裂解作为关键步骤，我们已经完成了二甲醚A和B的C-1–C-15片段的合成。此外，我们使用类似的策略构建了双硒化物E的α，β-不饱和内酯部分。
• Studies on the synthesis of the core structures of the antitumor agents neocarzinostatin, kedarcidin, C-1027 and maduropeptin
  作者：Philip Magnus、Rich Carter、Martin Davies、Jason Elliott、Thomas Pitterna

  DOI：10.1016/0040-4020(96)00283-9

  日期：1996.4

  The bicyclo[7.3.0]dodecadiyne core structure of the antitumor agents neocarzinostatin, kedarcidin, C-1027 and maduropeptin can be readily constructed by an intramolecular aldol reaction to form the bond only if the C-6,7 triple bond is complexed as its η2Co2(CO)6-acetylene adduct.

  仅当C-6,7三键复合时，分子内的醛醇缩合反应才能轻松地构建抗肿瘤药新carzinostatin，kedarcidin，C-1027和maduropeptin的双环[7.3.0]十二碳芯结构。η 2共2（CO）6 -acetylene加合物。
• Synthesis and Structure−Activity Relationships of a New Series of Retinoid-Related Biphenyl-4-ylacrylic Acids Endowed with Antiproliferative and Proapoptotic Activity
  作者：Raffaella Cincinelli、Sabrina Dallavalle、Raffaella Nannei、Serena Carella、Daniele De Zani、Lucio Merlini、Sergio Penco、Enrico Garattini、Giuseppe Giannini、Claudio Pisano、Loredana Vesci、Paolo Carminati、Valentina Zuco、Chiara Zanchi、Franco Zunino

  DOI：10.1021/jm049440h

  日期：2005.7.1

  Atypical retinoids (AR) represent a class of proapoptotic agents with promising potential in the treatment of neoplastic diseases. In the present work 4'-hydroxybiphenyl-4-ylacrylic acids were studied as a novel series of AR. The synthesized compounds were evaluated for their antiproliferative activity in a human promyelocytic leukemia cell line (NB4) and in an ovarian carcinoma cell system including IGROV-1, carrying a functional wild-type p53, and a cisplatin-resistant subline, IGROV-1/Pt-1. The presence of a bulky lipophilic group at position 3' (adamantan-1-yl being the best) and the E configuration of the acrylic moiety appear essential for activity below 1 mu M. No substitution on the rings or on the double bond improved the activity. A qualitative correlation between the log P and molecular volume of the 3'-substituent and the antiproliferative activity was found. From the study of a few selected compounds, it appears that the presence of the carboxylic group is an essential requirement for apoptogenic properties but not for antiproliferative activity, this being maintained in amide derivatives. On the other hand, compounds able to induce apoptosis produced a detectable level of genotoxic damage. This observation supports the hypothesis that the genotoxic stress is a critical event mediating apoptosis induction by compounds of this class. Among the compounds investigated, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (2) was chosen for further investigation.