(R)-1-hydroxy-1-(naphthalen-2-yl)propan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-1-hydroxy-1-(naphthalen-2-yl)propan-2-one
• 英文别名: (R)-1-hydroxy-1-(2-naphthyl)-2-propanone；(1R)-1-hydroxy-1-naphthalen-2-ylpropan-2-one
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: GGJCEUHNXGRAOS-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(萘-2-基)丙-2-炔-1-醇 在 lithium aluminium tetrahydride 、 三氯化铝 、 α-AD mix {K4[Fe(CN)6], OsO4, Na2CO3, (DHQ)2-PHAL} 作用下， 生成 (R)-1-hydroxy-1-(naphthalen-2-yl)propan-2-one
  参考文献：
  名称：

  亚烯的不对称二羟基化

  摘要：

  为了合成手性α-羟基酮，我们使用了烯丙基的不对称二羟基化（AD）。该方法已经应用于几种芳基取代的烯。我们发现芳环上的给电子基团增加了反应效率。

  DOI：

  10.1016/j.tetlet.2004.03.037

文献信息

• Catalytic Scope of the Thiamine-Dependent Multifunctional Enzyme Cyclohexane-1,2-dione Hydrolase
  作者：Sabrina Loschonsky、Simon Waltzer、Sonja Fraas、Tobias Wacker、Susana L. A. Andrade、Peter M. H. Kroneck、Michael Müller

  DOI：10.1002/cbic.201300673

  日期：2014.2.10

  cyclohexane‐1,2‐dione hydrolase (CDH) catalyzes the asymmetric cross‐benzoin reaction of aromatic aldehydes and pyruvate (up to quantitative conversion and 92–99 % ee). Notably, CDH accepts several aldehydes, such as hydroxybenzaldehydes, nitrobenzaldehydes, and naphthaldehydes; previously, these have only in rare cases been known as substrates of other thiamine‐dependent enzymes.

  归并在一起：重组环己烷-1，2-二酮水解酶（CDH）催化芳香醛和丙酮酸的不对称交叉安息香反应（达到定量转化率和92–99％ee）。值得注意的是，CDH可以接受多种醛，例如羟基苯甲醛，硝基苯甲醛和萘醛。以前，这些仅在极少数情况下被称为其他硫胺素依赖性酶的底物。
• Sesquiterpene derivatives and their use in inflammation or cancer treatment
  申请人：Academia Sinica

  公开号：US10238631B2

  公开（公告）日：2019-03-26

  A new class of sesquiterpene derivative useful for treating cancerous and inflammatory diseases are disclosed. These deoxyelephantopin derivatives are effective in suppressing proliferation, migration, mobility, invasion, growth, and/or metastasis of cancer cells in a patient, or useful for enhancing an anti-proliferative effect of another anti-cancer drug on cancer cells when treating a patient, or for sensitizing and/or enhancing an anti-cancer effect of a gluthathione synthesis blocker on inhibition of triple negative breast cancer cell activity, or for treatment and/or prophylaxis of lipopolysaccharide-stimulated inflammatory response in a patient, or for all of the above. Also disclosed are methods of preparing the deoxyelephantopin derivatives.

  本研究公开了一类可用于治疗癌症和炎症性疾病的新型倍半萜衍生物。这些脱氧苦艾素衍生物可有效抑制患者体内癌细胞的增殖、迁移、移动、侵袭、生长和/或转移，或在治疗患者时增强另一种抗癌药物对癌细胞的抗增殖作用、或用于增敏和/或增强谷胱甘肽合成阻滞剂对抑制三阴性乳腺癌细胞活性的抗癌作用，或用于治疗和/或预防患者体内脂多糖刺激的炎症反应，或用于上述所有用途。还公开了制备脱氧苦参碱衍生物的方法。
• NOVEL SESQUITERPENE DERIVATIVES AND THEIR USE IN INFLAMMATION OR CANCER TREATMENT
  申请人：Academia Sinica

  公开号：US20170182001A1

  公开（公告）日：2017-06-29

  A new class of sesquiterpene derivative useful for treating cancerous and inflammatory diseases are disclosed. These deoxyelephantopin derivatives are effective in suppressing proliferation, migration, mobility, invasion, growth, and/or metastasis of cancer cells in a patient, or useful for enhancing an anti-proliferative effect of another anti-cancer drug on cancer cells when treating a patient, or for sensitizing and/or enhancing an anti-cancer effect of a gluthathione synthesis blocker on inhibition of triple negative breast cancer cell activity, or for treatment and/or prophylaxis of lipopolysaccharide-stimulated inflammatory response in a patient, or for all of the above. Also disclosed are methods of preparing the deoxyelephantopin derivatives.
• Identification and Characterization of Thiamine Diphosphate‐Dependent Lyases with an Unusual CDG Motif
  作者：Lucrezia Lanza、Fabian Rabe von Pappenheim、Daniela Bjarnesen、Camilla Leogrande、Alexandra Paul、Leonhard Krug、Kai Tittmann、Michael Müller

  DOI：10.1002/anie.202404045

  日期：2024.8.19

  The thiamine diphosphate (ThDP)‐binding motif, characterized by the canonical GDG(X)24‐27N sequence, is highly conserved among ThDP‐dependent enzymes. We investigated a ThDP‐dependent lyase (JanthE from Janthinobacterium sp. HH01) with an unusual cysteine (C458) replacing the first glycine of this motif. We found that JanthE has a high substrate promiscuity accepting long aliphatic α‐keto acids as donors. Sterically hindered aromatic aldehydes or non‐activated ketones are acceptor substrates, giving access to a variety of secondary and tertiary alcohols as carboligation products. The crystal structure solved at a resolution of 1.9 Å reveals that C458 is not primarily involved in the cofactor binding as previously thought for the canonical glycine. Instead, it coordinates methionine 406, thus ensuring the integrity of the active site and the enzyme activity. We further determined the long‐sought genuine tetrahedral intermediates formed with pyruvate and 2‐oxo‐butyrate in the pre‐decarboxylation states and unravel atomic details for their stabilization in the active site. Collectively, we unravel an unexpected role for the first residue of the ThDP‐binding motif and unlock a family of lyases able to perform valuable carboligation reactions.