(S)-3-hydroxy-3-methylchroman-4-one | 127184-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-3-hydroxy-3-methylchroman-4-one
• 英文别名: (S)-3-hydroxy-3-methyl-4-chromanone；(3S)-3-hydroxy-3-methyl-2H-chromen-4-one
• CAS: 127184-08-1
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: CYPTVRVQDISABX-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(1,3-dioxan-2-yl)phenol 在 盐酸 、 四甲基乙二胺 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 、 甲苯 为溶剂， 反应 18.5h， 生成 (S)-3-hydroxy-3-methylchroman-4-one
  参考文献：
  名称：

  Modified Chiral Triazolium Salts for Enantioselective Benzoin Cyclization of Enolizable Keto-Aldehydes:  Synthesis of (+)-Sappanone B

  摘要：

  Asymmetric synthesis of (+)-sappanone B (1), a natural product with a 3-hydroxy chromanone structure, was achieved via enantioselective benzoin cyclization by using a modified Rovis catalyst and triethylamine. This catalyst enabled the successful benzoin cyclization of readily enolizable keto-aldehydes.

  DOI：

  10.1021/ol070929p

文献信息

• Solvent-Free Benzoin and Stetter Reactions with a Small Amount of NHC Catalyst in the Liquid or Semisolid State
  作者：Tadashi Ema、Yoshiko Nanjo、Sho Shiratori、Yuta Terao、Ryo Kimura

  DOI：10.1021/acs.orglett.6b03115

  日期：2016.11.4

  The intermolecular or intramolecular asymmetric benzoin reaction was catalyzed by a small amount of N-heterocyclic carbene (NHC) (0.2–1 mol %) under solvent-free conditions. The solvent-free intramolecular asymmetric Stetter reaction also proceeded efficiently with NHC (0.2–1 mol %). In some cases, even solid-to-solid or solid-to-liquid conversions took place with low catalyst loading (0.2–1 mol %)

  在无溶剂条件下，少量的N-杂环卡宾（NHC）（0.2-1 mol％）催化分子间或分子内不对称安息香反应。使用NHC（0.2–1 mol％），无溶剂的分子内不对称Stetter反应也能有效地进行。在某些情况下，即使在催化剂负载量较低（0.2–1摩尔％）的情况下，也可以进行固-固或固-液转化。
• Studies Towards the Stereoselective α-Hydroxylation of Flavanones. Biosynthetic Significance
  作者：Zola-Michéle Border、Charlene Marais、Barend C. B. Bezuidenhoudt、Jacobus A. Steenkamp

  DOI：10.1071/ch07325

  日期：——

  The enolates of various propiophenones, chromanones, and also analogues of naturally occurring flavanones were stereoselectively hydroxylated at the α-position, by employing commercially available enantiopure oxaziridines, to afford the desired α-hydroxylated target molecules in good to exceptional stereoselectivities and in moderate to good chemical yields. A mechanistic rationale is presented to account for the stereoselectivities achieved. These in vitro results were tentatively related to the stereoselective biosynthesis of enantio-enriched dihydroflavonols while questions were raised about the authenticity of certain natural compounds.

  通过使用市场上可买到的对映体纯噁嗪基里胺，对各种苯丙酮、色酮以及天然黄烷酮类似物的烯醇化物在α位进行立体选择性羟基化，以良好至特殊的立体选择性和中等至良好的化学收率得到所需的α-羟基化目标分子。本研究提出了一种机理原理来解释所实现的立体选择性。这些体外研究结果与对映体丰富的二氢黄酮醇的立体选择性生物合成初步相关，同时也对某些天然化合物的真实性提出了质疑。
• Asymmetric Synthesis of Chromanones via N-Heterocyclic Carbene Catalyzed Intramolecular Crossed-Benzoin Reactions
  作者：Dieter Enders、Oliver Niemeier、Gerhard Raabe

  DOI：10.1055/s-2006-950403

  日期：2006.9

  The enantioselective synthesis of 3-hydroxy-4-chromanones bearing a quaternary stereocenter via an N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reaction is described.

  描述了通过 N-杂环卡宾催化的分子内交叉安息香反应对映选择性合成带有四元立体中心的 3-羟基-4-色满酮。
• Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1<i>R</i>)-Camphor-Derived <i>N</i>-Heterocyclic Carbenes
  作者：Zbigniew Rafiński、Anna Kozakiewicz

  DOI：10.1021/acs.joc.5b01029

  日期：2015.8.7

  A catalytic asymmetric intramolecular crossed-benzoin reaction for the synthesis of chromanones by novel camphor-derived N-heterocyclic carbenes is described. The corresponding chromanones bearing quaternary stereogenic centers were isolated in high yields with high to excellent enantioselectivity.
• Enantioselective synthesis of tertiary .alpha.-hydroxy carbonyl compounds using [(8,8-dichlorocamphoryl)sulfonyl]oxaziridine
  作者：Franklin A. Davis、Michael C. Weismiller

  DOI：10.1021/jo00299a007

  日期：1990.6