(R)-3-(2-Hydroxy-ethyl)-indan-1-one | 877400-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-3-(2-Hydroxy-ethyl)-indan-1-one
• 英文别名: (3R)-3-(2-hydroxyethyl)-2,3-dihydroinden-1-one
• CAS: 877400-05-0
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: SJVHIDZZXXPLLY-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (R)-3-(2-Hydroxy-ethyl)-indan-1-one 在 咪唑 、 硼酸三乙酯 、 锌 作用下， 以 四氢呋喃 为溶剂， 生成 [(R)-1-Hydroxy-3-(2-triisopropylsilanyloxy-ethyl)-indan-1-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors possessing augmented P2′ side chains

  摘要：

  A series of monopyrrolinone-based HIV-1 protease inhibitors possessing rationally designed P2' side chains have been synthesized and evaluated for activity against wild-type HIV-1 protease. The most potent inhibitor displays subnanomolar potency in vitro for the wild-type HIV-1 protease. Additionally, the monopyrrolinone inhibitors retain potency in cellular assays against clinically significant mutant forms of the virus. X-ray structures of these inhibitors bound in the wild-type enzyme reveal important insights into the observed biological activity.

  DOI：

  10.1016/j.bmcl.2005.11.011
• 作为产物：
  描述：

  (R)-3-Allyl-indan-1-one 在 臭氧 、 lithium tri-t-butoxyaluminum hydride 、 三苯基膦 作用下， 生成 (R)-3-(2-Hydroxy-ethyl)-indan-1-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors possessing augmented P2′ side chains

  摘要：

  A series of monopyrrolinone-based HIV-1 protease inhibitors possessing rationally designed P2' side chains have been synthesized and evaluated for activity against wild-type HIV-1 protease. The most potent inhibitor displays subnanomolar potency in vitro for the wild-type HIV-1 protease. Additionally, the monopyrrolinone inhibitors retain potency in cellular assays against clinically significant mutant forms of the virus. X-ray structures of these inhibitors bound in the wild-type enzyme reveal important insights into the observed biological activity.

  DOI：

  10.1016/j.bmcl.2005.11.011

文献信息

• Hydroacylation of 2-Vinyl Benzaldehyde Systems:  An Efficient Method for the Synthesis of Chiral 3-Substituted Indanones
  作者：Kousik Kundu、James V. McCullagh、Andrew T. Morehead

  DOI：10.1021/ja0564416

  日期：2005.11.23

  Asymmetric rhodium-catalyzed hydroacylation has been utilized in the synthesis of 3-substituted indanones with high conversions and enantioselectivity. The hydroacylation reaction of 2-vinyl benzaldehyde had been previously reported to give a low yield of indanone and an unidentified product. We have identified this compound as a dimer of the starting material. Substitution at the alpha-position of

  不对称铑催化加氢酰化已用于合成具有高转化率和对映选择性的 3-取代茚满酮。之前曾报道过 2-乙烯基苯甲醛的加氢酰化反应会产生低产率的茚满酮和未鉴定的产物。我们已将此化合物鉴定为起始材料的二聚体。在 2-乙烯基苯甲醛底物的 α 位取代可阻止竞争性二聚反应，并使反应以通常大于 90% 的产率进行。在大多数情况下，使用 BINAP 作为手性配体可获得良好的化学产率和大于 95% 的对映选择性。
• Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors possessing augmented P2′ side chains
  作者：Amos B. Smith、Adam K. Charnley、Hironori Harada、Jason J. Beiger、Louis-David Cantin、Craig S. Kenesky、Ralph Hirschmann、Sanjeev Munshi、David B. Olsen、Mark W. Stahlhut、William A. Schleif、Lawrence C. Kuo

  DOI：10.1016/j.bmcl.2005.11.011

  日期：2006.2

  A series of monopyrrolinone-based HIV-1 protease inhibitors possessing rationally designed P2' side chains have been synthesized and evaluated for activity against wild-type HIV-1 protease. The most potent inhibitor displays subnanomolar potency in vitro for the wild-type HIV-1 protease. Additionally, the monopyrrolinone inhibitors retain potency in cellular assays against clinically significant mutant forms of the virus. X-ray structures of these inhibitors bound in the wild-type enzyme reveal important insights into the observed biological activity.