tricarbonyl(η⁶-2-phenyl-1,3-dioxolane)chromium(0) | 122114-10-7

• 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: tricarbonyl(η⁶-2-phenyl-1,3-dioxolane)chromium(0)
• 英文别名: tricarbonyl[2-(η(6)-phenyl)-1,3-dioxolane]chromium；dioxobenzaldehyde chromium tricarbonyl；Carbon monoxide;chromium;2-phenyl-1,3-dioxolane
• CAS: 122114-10-7
• 化学式: C₁₂H₁₀CrO₅
• 分子量: 286.204
• InChiKey: IPZWPFLUNCGDGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tricarbonyl(η⁶-2-phenyl-1,3-dioxolane)chromium(0) 在 p-toluenesulphonic acid 作用下， 以 丙酮 为溶剂， 以76%的产率得到[(1,2,3,4,5,6-η)benzaldehyde]tricarbonylchromium
  参考文献：
  名称：

  一系列环取代的芳烃铬二羰基三苯基膦配合物的31 P化学位移和羰基拉伸力常数与取代基常数的相关性

  摘要：

  制备了十四个单取代的芳烃三羰基铬和芳烃铬二羰基三苯基膦配合物，并通过IR和NMR光谱表征。已经计算出所有化合物的羰基拉伸力常数。芳烃铬三羰基配合物的拉伸力常数与一系列取代基常数的相关性与早期研究报道的一致。类似地，将芳烃铬二羰基三苯基膦配合物的拉伸力常数和31 P化学位移与相同系列的取代基常数进行了比较，发现其趋势类似于先前观察到的趋势。

  DOI：

  10.1016/s0277-5387(00)80388-5
• 作为产物：
  描述：

  2-苯基-1,3-二四氢呋喃 生成 tricarbonyl(η⁶-2-phenyl-1,3-dioxolane)chromium(0)
  参考文献：
  名称：

  DAVIES, STEPHEN G.;GOODFELLOW, CRAIG L., SYNLETT,(1989) N, C. 59-62

  摘要：

  DOI：

文献信息

• Asymmetric Synthesis of Planar Chiral (Arene)tricarbonylchromium Complexes via Enantioselective Deprotonation by Conformationally Constrained Chiral Lithium-Amide Bases
  作者：Sandrine Pache、Candice Botuha、Roberto Franz、E. Peter Kündig、Jacques Einhorn

  DOI：10.1002/1522-2675(20000906)83:9<2436::aid-hlca2436>3.0.co;2-n

  日期：2000.9.6

  addition reactions with eight chiral Li-amide bases, 1 - 8, and five [Cr(arene)(CO)3] complexes, 9 - 13, were investigated. Restriction of conformational freedom in the chiral Li-amide base Li-1, in general, did not result in an increase in asymmetric induction. A new route to enantiomerically enriched (75 - 92%) planar chiral ortho-substituted benzaldehyde complexes via enantioselective lithiation of

  研究了与八个手性锂酰胺碱基 1-8 和五个 [Cr(arene)(CO)3] 配合物 9-13 的对映选择性锂化/亲电加成反应。一般来说，限制手性锂酰胺基 Li-1 中的构象自由度不会导致不对称诱导的增加。报道了一种通过苯扎亚胺配合物 16 和 17 的对映选择性锂化制备对映体富集 (75-92%) 平面手性邻位取代苯甲醛配合物的新途径。在 (1S)-对映异构体系列的邻取代苯甲醛配合物 18a - d 中，除了三甲基甲锡烷基衍生物 18b 之外，发现比旋光度的符号 [a] 是正的。这被解释为醛基的反向构象。
• Two-step synthesis of homochiral monoaminals of tricarbonylphthalaldehydechromium complex
  作者：Françoise Rose-Munch、Vanessa Gagliardini、Anne Perrotey、Jean-Philippe Tranchier、Eric Rose、Pierre Mangeney、Alexandre Alexakis、Tonis Kanger、Jacqueline Vaissermann

  DOI：10.1039/a906043j

  日期：——

  Tricarbonylphthalaldehydechromium complex can be prepared using a ‘one pot’ procedure starting from tricarbonylbenzenechromium: the protection of one aldehyde function by chiral diamines leads to the formation of two diastereoisomers of the monoaminal of the phthlaldehyde complexes, efficient precursors of enantiopure ortho-substituted alkenyl arene complexes.

  三羰基邻苯二甲醛铬络合物可通过 "一锅式 "程序从三羰基苯铬开始制备：通过手性二胺对一个醛功能的保护，可形成邻苯二甲醛络合物单氨基的两种非对映异构体，它们是对映体纯正取代烯基炔络合物的有效前体。
• (R)- and (S)-enantioselective lithiation of (arene)tricarbonylchromium acetal complexes with chiral alkyllithiums
  作者：Michael J. Siwek、James R. Green

  DOI：10.1039/cc9960002359

  日期：——

  The lithiation of (arene)tricarbonylchromium acetal complexes with the organolithium reagents derived from (1R)-menthyl chloride and (1R)-8-phenylmenthyl chloride occurs at the pro-R site (up to 70% ee) and the pro-S(up to 80% ee), respectively.

  (芳烃)三羰基铬缩醛配合物与源自(1R)-氯薄荷和(1R)-8-苯基薄荷氯的有机锂试剂的锂化发生在pro-R位点（高达70% ee）和pro-S（分别高达 80% ee)。
• Synthesis and reactions of [(((η6)-2-acylaryl)-C,O)tetracarbonylmanganese]-tricarbonylchromium complexes: enhancement of diastereoselection during cyclopentaannulation
  作者：George R Clark、Michael R Metzler、Giles Whitaker、Paul D Woodgate

  DOI：10.1016/0022-328x(95)05964-q

  日期：1996.5

  Cyclomanganation reactions of [(eta(6))-acylaryl]tricarbonylchromium complexes have been investigated, Three novel heterobimetallic complexes have been synthesised in moderate to good yield, with one being characterised by X-ray crystallography. Several modes of activating these bimetallic complexes towards coupling reactions with substituted alkenes and alkynes were investigated, including oxidative decarbonylation at room temperature, and thermal promotion. The stereochemistry of one of the cyclopentaannulated adducts has been established by X-ray crystallography. Thermal displacement of one of the CO ligands of the bimetallic complex 27 in the presence of PPh(3) afforded a single adduct, the structure of which was established by X-ray crystallography. The chemistry of this novel bimetallic system was investigated.
• A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs
  作者：Shoulei Wang、Carles Rodríguez-Escrich、Xinyuan Fan、Miquel A. Pericàs

  DOI：10.1016/j.tet.2018.04.022

  日期：2018.7

  Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde into eta(6)-benzaldehyde Cr(CO)(3) circumvents this limitation. Asymmetric synthesis of (R)-Phenoperidine, as well as formal syntheses of (R)Fluoxetine and (R)-Atomoxetine, illustrate the benefits of this strategy. (C) 2018 Elsevier Ltd. All rights reserved.