3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane | 218439-10-2

• 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: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane
• 英文别名: (S)-4-benzyl-3-[2-(triphenylphospanylidene)acetyl]oxazolidin-2-one；(S)-4-benzyl-2-oxazolidinyl(triphenylphosphoranylidene)acetate；(S)-4-benzyl-3-(2-(triphenylphosphaneylidene)acetyl)oxazolidin-2-one；(4S)-4-benzyl-3-[2-(triphenyl-lambda5-phosphanylidene)acetyl]-1,3-oxazolidin-2-one；(4S)-4-benzyl-3-[2-(triphenyl-λ5-phosphanylidene)acetyl]-1,3-oxazolidin-2-one
• CAS: 218439-10-2
• 化学式: C₃₀H₂₆NO₃P
• 分子量: 479.515
• InChiKey: QULZMEKUYFHEDF-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane 以 乙醚 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (S)-3-[(E)-3-(4-Amino-cyclohexyl)-acryloyl]-4-benzyl-oxazolidin-2-one; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Noguchi, Hirohide; Aoyama, Toyohiko; Shioiri, Takayuki, Heterocycles, 2002, vol. 58, p. 471 - 504

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-4-苄基-3-(2-溴乙酰基)-1,3-恶唑烷-2-酮 在 sodium hydroxide 作用下， 以 乙醚 、 苯 为溶剂， 反应 2.0h， 生成 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane
  参考文献：
  名称：

  A Rapid Access to Both Enantiomers of 1,2,3,4-Tetranor B-Trienic 18,18,18-Trifluorosteroids. The First Enantiocontrolled Total Synthesis of 18,18,18-Trifluorosteroids

  摘要：

  Chiral A-tetranor B-trienic 18,18,18-trifluorosteroid 2a and its enantiomer 1a were synthesised by the thermolysis of chiral olefinic benzocyclobutenes 7b and 7a which were in turn prepared by the aldol reaction of chiral oxazolidinone 5 and 11 with 2-(4-methoxybenzocyclobutenyl-1)-acetaldehyde as a key step. The compound 1a was then transformed into 18,18,18-trifluorosteroid 9 via the ketone 13 and the diketone 14.

  DOI：

  10.1021/jo00108a022

文献信息

• Enantioselective Total Synthesis of RQN-18690A (18-Deoxyherboxidiene)
  作者：Yasunobu Matsumoto、Kazuhiro Hibino、Masahiro Yonaga、Hideaki Kakeya、Yujiro Hayashi

  DOI：10.1021/acs.orglett.6b01524

  日期：2016.7.15

  The first total synthesis of RQN-18690A (18-deoxyherboxidiene) and the determination of its absolute stereochemical configuration are described. The synthesis features an organocatalytic aldol reaction for the first step, 1,4- and 1,2- dual reductions of α,β-unsaturated δ-lactone followed by a domino reaction in a one-pot operation, and diastereoselective epoxidation with kinetic resolution.

  描述了RQN-18690A（18-脱氧herboxidiene）的第一个全合成及其绝对立体化学构型的确定。该合成的第一步是有机催化的羟醛反应，α，β-不饱和δ-内酯的1,4-和1,2-双重还原，然后在一个反应​​釜中进行多米诺反应以及具有动力学拆分能力的非对映选择性环氧化。
• Stereoselective Visible‐Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings
  作者：Fabrizio Medici、Simonetta Resta、Piero Presenti、Lucia Caruso、Alessandra Puglisi、Laura Raimondi、Sergio Rossi、Maurizio Benaglia

  DOI：10.1002/ejoc.202100397

  日期：2021.8.26

  An efficient protocol for the in-flow synthesis of enantiomerically enriched functionalized cyclopentane rings has been developed. By exploiting Evans’ oxazolidinones, the stereoselective light-driven cyclization of bisenones in a coil photoreactor affords, after the removal of the chiral auxiliary, an enantiomerically enriched cyclopentane. The cyclization was also successfully realized in a 3D-printed

  已经开发了一种有效的对映体富集功能化环戊烷环的流入合成方案。通过利用 Evans 的恶唑烷酮，双烯酮在线圈光反应器中的立体选择性光驱动环化在去除手性助剂后提供了对映体富集的环戊烷。环化也在 3D 打印的介观反应器中成功实现。
• Synthesis of the Four Stereoisomers of 2,6-Dimethyloctane-1,8-dioic Acid, a Component of the Copulation Release Pheromone of the Cowpea Weevil,<i>Callosobruchus maculatus</i>
  作者：Tomonori NAKAI、Arata YAJIMA、Kazuaki AKASAKA、Takayuki KAIHOKU、Miki OHTAKI、Tomoo NUKADA、Hiroshi OHRUI、Goro YABUTA

  DOI：10.1271/bbb.69.2401

  日期：2005.1

  A diastereomeric mixture and the four stereoisomers of 2,6-dimethyloctane-1,8-dioic acid (2), a copulation release pheromone of the cowpea weevil, Callosobruchus maculatus, were synthesized. The stereoisomeric purities of the four synthetic isomers of 2 were determined by the HPLC analyses of their bis-2-(2,3-anthracenedicarboximide)-1-cyclohexyl esters.

  合成了豇豆象鼻虫（Callosobruchus maculatus）的一种交配释放信息素--2,6-二甲基辛烷-1,8-二酸（2）的非对映混合物和四种立体异构体。通过对其双-2-(2,3-蒽二甲酰亚胺)-1-环己基酯进行高效液相色谱分析，确定了 2 的四种合成异构体的立体异构纯度。
• Synthetic Study on a 26-Membered Macrolide, Amphidinolide B: Synthesis of the C₁—C₁₃Fragment
  作者：Katsuhide Ohi、Kyoko Shima、Kozue Hamada、Yoshio Saito、Naoki Yamada、Shigeru Ohba、Shigeru Nishiyama

  DOI：10.1246/bcsj.71.2433

  日期：1998.10

  The C1—C13 fragment of amphidinolide B (1) was synthesized from D-erythrose (3). The Evans alkylation reaction protocol allowed the introduction of the stereogenic center at the C11 position, which was unambiguously confirmed by a single X-ray crystallographic analysis.

  由 D-赤藓酮（3）合成了蚜虫内酯 B 的 C1-C13 片段（1）。埃文斯烷基化反应方案允许在 C11 位置引入立体中心，这一点通过一次 X 射线晶体分析得到了明确证实。
• Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin
  作者：Emma K. Davison、Jared L. Freeman、Wanli Zhang、William M. Wuest、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/acs.orglett.0c01913

  日期：2020.7.17

  The first total synthesis of the potent antibiotic anthracimycin was achieved in 20 steps. The synthesis features an intramolecular Diels–Alder reaction to forge the trans-decalin moiety, and an unprecedented aldol reaction using a complex β-ketoester to provide the tricarbonyl motif. A Stork–Zhao olefination and Grubbs ring closing metathesis delivered the E/Z-diene and forged the macrocycle. The

  强效抗生素蒽霉素的首次全合成经过 20 个步骤实现。该合成的特点是通过分子内狄尔斯-阿尔德反应形成反式十氢化萘部分，以及使用复杂的β-酮酯来提供三羰基基序的前所未有的羟醛反应。Stork-Zhao 烯化和 Grubbs 闭环复分解产生了E / Z -二烯并形成了大环。C2构型通过碱基介导的差向异构化设置，从而提供对(-)-蒽霉素的接触。