(R)-3-(benzyloxy)pentanal | 153077-88-4

• 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: (R)-3-(benzyloxy)pentanal
• 英文别名: (3R)-3-phenylmethoxypentanal
• CAS: 153077-88-4
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: SIUPFVSSODOULT-GFCCVEGCSA-N

物化性质

• 沸点：
  289.4±15.0 °C(predicted)
• 密度：
  0.999±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (R)-3-(benzyloxy)pentanal 在 palladium on activated charcoal sodium tetrahydroborate 、 air 、 三乙基硼 、 三(三甲基硅基)硅烷 、 氢气 、 4-甲基苯磺酸吡啶 、 四氯化钛 、 臭氧 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 21.5h， 生成 (+)-methyl homononactate
  参考文献：
  名称：

  Feigrisolide C:  Structural Revision and Synthesis

  摘要：

  The original macrodiolide structure proposed for feigrisolide C was incorrect. The true structure of feigrisolide C was identified as (2'S,3'S,6'R,8'R)-homononactoyl (2R,3R,6S,8S)-nonactic acid, which was confirmed by total synthesis.

  DOI：

  10.1021/jo051107d
• 作为产物：
  描述：

  (-)-(R)-3-羟基戊酸甲酯 在 lithium aluminium tetrahydride 、 pyridine-SO3 complex 、 三氟甲磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 1.5h， 生成 (R)-3-(benzyloxy)pentanal
  参考文献：
  名称：

  Feigrisolide C:  Structural Revision and Synthesis

  摘要：

  The original macrodiolide structure proposed for feigrisolide C was incorrect. The true structure of feigrisolide C was identified as (2'S,3'S,6'R,8'R)-homononactoyl (2R,3R,6S,8S)-nonactic acid, which was confirmed by total synthesis.

  DOI：

  10.1021/jo051107d

文献信息

• [EN] CYTOTOXIC ACTIN-TARGETING COMPOUNDS<br/>[FR] COMPOSÉS CYTOTOXIQUES CIBLANT L'ACTINE
  申请人：UNIV KINGSTON

  公开号：WO2019033219A1

  公开（公告）日：2019-02-21

  A class of compounds useful in pharmaceutical compositions and methods for treating or preventing cancer is described. Analogs of Mycalolide B have been prepared and tested in breast and ovarian cancer cell lines. The compounds show utility for inhibition of survival and proliferation of tumor cells. The compounds have been shown to disrupt actin.

  描述了一类在制药组合物和治疗或预防癌症方法中有用的化合物。已经制备并在乳腺癌和卵巢癌细胞系中测试了Mycalolide B的类似物。这些化合物显示出抑制肿瘤细胞存活和增殖的效用。已经证明这些化合物会破坏肌动蛋白。
• Cytotoxic actin-targeting compounds
  申请人：Queen's University at Kingston

  公开号：US11369594B2

  公开（公告）日：2022-06-28

  A class of compounds useful in pharmaceutical compositions and methods for treating or preventing cancer is described. Analogs of Mycalolide B have been prepared and tested in breast and ovarian cancer cell lines. The compounds show utility for inhibition of survival and proliferation of tumor cells. The compounds have been shown to disrupt actin.

  本文描述了一类可用于治疗或预防癌症的药物组合物和方法的化合物。制备了霉酚酸内酯 B 的类似物，并在乳腺癌和卵巢癌细胞系中进行了测试。这些化合物显示出抑制肿瘤细胞存活和增殖的作用。研究表明，这些化合物能破坏肌动蛋白。
• A new catalytic asymmetric approach to polyfunctional aldol products mediated by zinc organometallics
  作者：Paul Knochel、Walter Brieden、Michael J. Rozema、Christina Eisenberg

  DOI：10.1016/s0040-4039(00)73804-4

  日期：1993.9

  The catalytic asymmetric addition of functionalized dialkylzincs to beta-alkoxyaldehydes provides after a short sequence of functional group interconversions aldol products in 40-99% ee. Their stereoselective transformation to either syn- or anti-1,3-diols has been performed.
• Cytotoxic Actin-Targeting Compounds
  申请人：Queen's University at Kingston

  公开号：US20200306233A1

  公开（公告）日：2020-10-01

  A class of compounds useful in pharmaceutical compositions and methods for treating or preventing cancer is described. Analogs of Mycalolide B have been prepared and tested in breast and ovarian cancer cell lines. The compounds show utility for inhibition of survival and proliferation of tumor cells. The compounds have been shown to disrupt actin.
• Feigrisolide C:  Structural Revision and Synthesis
  作者：Woo Han Kim、Jae Hoon Jung、Eun Lee

  DOI：10.1021/jo051107d

  日期：2005.9.1

  The original macrodiolide structure proposed for feigrisolide C was incorrect. The true structure of feigrisolide C was identified as (2'S,3'S,6'R,8'R)-homononactoyl (2R,3R,6S,8S)-nonactic acid, which was confirmed by total synthesis.