3-isopropyl-4-hydroxymethylcyclopent-2-en-1-one | 106237-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isopropyl-4-hydroxymethylcyclopent-2-en-1-one
• 英文别名: 3-isopropyl-4-hydroxymethylcyclopent-2-enone；4-(hydroxymethyl)-3-isopropylcyclopent-2-enone；4-(Hydroxymethyl)-3-propan-2-ylcyclopent-2-en-1-one
• CAS: 106237-67-6
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: XUTXISYISWLHIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-isopropyl-4-hydroxymethylcyclopent-2-en-1-one 在 咪唑 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  <p>Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds</p>

  摘要：

  Background: Neolaxiflorin B is derived from ent-kaurane like laxiflorin J and eriocalyxin B with a relatively low potency as an antitumor agent. During preliminary structure-activity relationship studies, the alpha,beta-unsaturated ketone (enone) system is an important active group.Methods: Seven neolaxiflorin B derivatives containing alpha,beta-unsaturated ketone moieties were synthesized. In vitro, activity was evaluated against three human tumor cell lines and a rat myogenic cell line (HepG2, NSCLC-H292, SNU-1040, and L6, respectively) by MTT assay.Results: Compound 15 appeared a promising antitumor lead due to its cytotoxic potency and relatively high selectivity, with an SI value of 13.14. Flow cytometry analysis was conducted to show that NSCLC-H292 cells were blocked in the G0/G1 phase in the presence of compound 15, thus inhibiting the proliferation of tumor cells.Conclusion: This study has revealed that compound 15 is a promising antitumor lead due to the cytotoxic potencies and the high selectivity it displayed when compared to natural counterparts.

  DOI：

  10.2147/dddt.s202345
• 作为产物：
  描述：

  3-(烯丙氧基)-3-甲基丁-1-炔 在 dicobalt hexacarbonyl 、 silica gel 作用下， 生成 3-isopropyl-4-hydroxymethylcyclopent-2-en-1-one
  参考文献：
  名称：

  吸附对烯丙基炔丙基醚钴合成3-氧杂双环[3.3.0] oct-5-en-7-one衍生物的效率的影响

  摘要：

  氧在吸附状态下的热解是促进烯丙基炔丙基醚的二钴六羰基配合物的Khand-Pauson环化为3-氧杂双环[3.3.0] oct-5-en-7-one的衍生物的温和且通用的方法。 。

  DOI：

  10.1016/s0040-4039(00)84228-8

文献信息

• Cyclization of Dicobalthexacarbonyl Complexes of Allyl Propargyl Ethers on the Surface of Chromatography Adsorbents. A Convenient Method for the Preparation of Substituted 3-Oxabicyclo[3.3.0]oct-5-en-7-one and 4-Hydroxymethyl-2-cyclopenten-1-one Derivatives from Common Precursors
  作者：W. A. Smit、S. O. Simonyan、V. A. Tarasov、G. S. Mikaelian、A. S. Gybin、I. I. Ibragimov、R. Caple、D. Froen、A. Kreager

  DOI：10.1055/s-1989-27296

  日期：——

  Allyl propargyl ethers serve as valuable precursors for short and efficient syntheses of the title compounds via an intramolecular [2 + 2 + 1] Khand-Pauson cyclization under the novel procedure of adsorption-promoted (dry state) conditions.

  丙烯基丙炔醚作为有价值的前体，通过一种新颖的吸附促进（干态）条件下的分子内 [2 + 2 + 1] Khand-Pauson 环化反应，为标题化合物的简短和高效合成提供了途径。
• Intramolecular cyclization of dicobalt hexacarbonyl complexes of allyl propyl ethers on adsorbent surfaces. A convenient mode of preparation of 3-oxabicyclo[3.3.0]octenes and 4-hydroxymethylcyclopentenone derivatives
  作者：V. A. Smit、S. O. Simonyan、V. A. Tarasov、A. S. Gybin、G. S. Mika�lyan、A. S. Shashkov、S. S. Mamyan、I. I. Ibragimov、R. K�ipl

  DOI：10.1007/bf00952633

  日期：1988.12
• SMIT, V. A.;SIMONYAN, S. O.;TARASOV, V. A.;GYBIN, A. S.;MIKAELYAN, G. S.;+, IZV. AN CCCP. CEP. XIM.,(1988) N2, S. 2802-2812
  作者：SMIT, V. A.、SIMONYAN, S. O.、TARASOV, V. A.、GYBIN, A. S.、MIKAELYAN, G. S.、+

  DOI：——

  日期：——
• SMIT V. A.; SIMONYAN S. O.; SHASHKOV A. S.; MAMYAN S. S.; TARASOV V. A.; +, IZV. AN CCCP. CEP. XIM.,(1987) N 1, 234-235
  作者：SMIT V. A.、 SIMONYAN S. O.、 SHASHKOV A. S.、 MAMYAN S. S.、 TARASOV V. A.、 +

  DOI：——

  日期：——
• Synthesis of 4-hydroxymethyl-2-cyclopentenones in the cyclization of dicobalt hexacarbonyl complexes of allyl propargyl ethers
  作者：V. A. Smit、S. O. Simonyan、A. S. Shashkov、S. S. Mamyan、V. A. Tarasov、I. I. Ibragimov

  DOI：10.1007/bf00953893

  日期：1987.1