(S)-5-(phenylmethoxy)-4-methylpentanal | 180692-68-6

• 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: (S)-5-(phenylmethoxy)-4-methylpentanal
• 英文别名: (S)-5-(benzyloxy)-4-methylpentanal；(S)-5-benzyloxy-4-methylpentanal；(4S)-4-methyl-5-phenylmethoxypentanal
• CAS: 180692-68-6
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: LITDPXRQVKGBBF-LBPRGKRZSA-N

物化性质

• 沸点：
  299.1±23.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (S)-5-(phenylmethoxy)-4-methylpentanal 在 草酰氯 、 双(三甲基硅烷基)氨基钾 、 臭氧 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 31.75h， 生成 (2R)-2-methyl-5-oxo-2-(phenylmethoxymethyl)heptanal
  参考文献：
  名称：

  Cyclohexenone Construction by Intramolecular Alkylidene C−H Insertion:  Synthesis of (+)-Cassiol

  摘要：

  We report new procedures for stereoselective cyclopentene and cyclohexenone construction employing the alkylidene carbene C-H insertion reaction. Described are diastereoselective insertion into methylene and enantiospecific insertion into methine C-H bonds. The latter case leads directly to the enantioselective synthesis of (+)-cassiol (1).

  DOI：

  10.1021/jo960973a
• 作为产物：
  描述：

  (2S)-2,6-dimethyl-5-hepten-1-ol 在 sodium hydride 、 臭氧 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (S)-5-(phenylmethoxy)-4-methylpentanal
  参考文献：
  名称：

  Cyclohexenone Construction by Intramolecular Alkylidene C−H Insertion:  Synthesis of (+)-Cassiol

  摘要：

  We report new procedures for stereoselective cyclopentene and cyclohexenone construction employing the alkylidene carbene C-H insertion reaction. Described are diastereoselective insertion into methylene and enantiospecific insertion into methine C-H bonds. The latter case leads directly to the enantioselective synthesis of (+)-cassiol (1).

  DOI：

  10.1021/jo960973a

文献信息

• Probing the Influence of an Allylic Methyl Group in Zearalenone Analogues on Binding to Hsp90
  作者：Christian Rink、Florenz Sasse、Asta Zubrienė、Daumantas Matulis、Martin E. Maier

  DOI：10.1002/chem.201001752

  日期：2010.12.27

  Carreira acetylide addition. Further routine steps led to the sulfones 29 and 45, respectively. After merging them with 2‐bromobenzaldehyde 9 in a Julia–Kocienski reaction, metalation, carboxylation, and protecting‐group manipulations gave the seco acids 35 and 49. By means of lactonization under Mitsunobu (alcohol activation) or Trost–Kita conditions (carboxyl activation), all four possible macrocyclic ketone

  通过有机合成用丙酸酯代替乙酸盐，制备了一系列具有烯丙基甲基的玉米赤霉烯酮类似物。为了合成类似物的脂肪族区域，我们使用了不对称烷基化反应生成了戊烯醇衍生物16和ent - 16。通过硼氢化反应，确保了相应的醛。通过加入Carreira乙炔化物将它们与2-戊炔醇衍生物23偶联。进一步的常规步骤分别导致了砜29和45。将它们与2-溴苯甲醛9合并后在一个朱莉娅- Kocienski所反应，金属化，羧化，和保护基团的操作，得到开环酸35和49。通过在Mitsunobu（酒精活化）或Trost-Kita条件（羧基活化）下进行内酯化，可以得到所有四种可能的大环酮立体异构体。总之，考虑各种保护基团的装饰品，获得和细胞毒性（L929小鼠成纤维细胞系）测试16点的类似物。而大多数类似物比玉米赤霉烯酮活性较低（IC 50 = 9.4μ中号），间苯二酚衍生物是可比的，用一种立体异构体（40b中）为稍微更活性（IC
• Highly stereoselective approach toward the synthesis of the macrolactone core of amphidinolide W
  作者：Debendra K. Mohapatra、Bhaskar Chatterjee、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2008.11.088

  日期：2009.2

  The diastereoselective synthesis of the macrolactone core of amphidinolide W was successfully accomplished using Evans’ asymmetric alkylation, Aldol reaction, Julia-Kocienski olefination, and Kita’s macrocyclization protocol.

  使用Evans的不对称烷基化，Aldol反应，Julia-Kocienski烯烃化反应和Kita的大环化方案成功完成了安非他命W的大内酯核的非对映选择性合成。
• Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid
  作者：Bhaskar Chatterjee、Dhananjoy Mondal、Smritilekha Bera

  DOI：10.1016/j.tetasy.2012.07.006

  日期：2012.8

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.
• Rationally Simplified Bistramide Analog Reversibly Targets Actin Polymerization and Inhibits Cancer Progression <i>in Vitro</i> and <i>in Vivo</i>
  作者：Syed Alipayam Rizvi、Song Liu、Zhonglei Chen、Colleen Skau、Matthew Pytynia、David R. Kovar、Steven J. Chmura、Sergey A. Kozmin

  DOI：10.1021/ja101811x

  日期：2010.6.2

  We describe structure-based design and chemical synthesis of a simplified analog of bistramide A, which potently and reversibly binds monomeric actin with a K(d) of 9.0 nM, depolymerizes filamentous actin in vitro and in A549 (nonsmall cell lung cancer) cells, inhibits growth of cancer cell lines in vitro at submicromolar concentrations, and significantly suppresses proliferation of A549 cells in a nude mice tumor xenograft model in terms of both tumor growth delay and average tumor volume. This study provides a conceptual framework for the design and development of new antiproliferative compounds that target cytoskeletal organization of cancer cells in vivo by a combination of reversible G-actin binding and effective F-actin severing.
• Synthesis of Bistramide A
  作者：Alexander V. Statsuk、Dong Liu、Sergey A. Kozmin

  DOI：10.1021/ja046588h

  日期：2004.8.1

  We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype delta. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening/cross-metathesis sequence employing a highly strained cyclopropenone acetal. The synthesis afforded the final target with the longest linear sequence of 15 steps and provided unambiguous structural determination of bistramide A, including assignment of the previously unknown C(37) stereochemistry.