(+/-)-Dihydrocitronellic acid chloride | 53838-48-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (+/-)-Dihydrocitronellic acid chloride
• 英文别名: 3,7-dimethyloctanoic acid chloride；dihydrocitronellic acid chloride；3,7-Dimethyloctanoyl chloride；(+/-)-2.6-dimethyl-octanoic acid-(8)-chloride；(+/-)-2.6-Dimethyl-octansaeure-(8)-chlorid；Tetrahydrogeraniumsaeure-chlorid
• CAS: 53838-48-5
• 化学式: C₁₀H₁₉ClO
• 分子量: 190.713
• InChiKey: RXNJHYGISMJXPH-UHFFFAOYSA-N

物化性质

• 沸点：
  215.7±8.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-Dihydrocitronellic acid chloride 在 ammonium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 3,7-dimethyloctanamide
  参考文献：
  名称：

  未活化 C(sp3)-H 键的可见光促进活化及其选择性三氟甲基硫醇化

  摘要：

  使用可见光对无处不在的 C(sp3)-H 键进行选择性功能化是有机合成中一个极具挑战性但理想的目标。此类工艺的开发依赖于合理设计和来自筛选技术等创新工具的偶然发现。应用基于机制的筛选策略，我们在此报告了光氧化还原介导的氢原子转移催化，用于选择性激活否则未激活的 C(sp3)-H 键，然后进行三氟甲基硫醇化，具有作为后期功能化工具的巨大潜力。这种方法的通用性是通过将三氟甲硫基以高选择性掺入大量 C(sp3)-H 键而不需要过量的有价值的底物来展示的。

  DOI：

  10.1021/jacs.6b09970
• 作为产物：
  描述：

  香叶酸 在 sodium hydroxide 、 palladium on activated charcoal 、 氯化亚砜 作用下， 生成 (+/-)-Dihydrocitronellic acid chloride
  参考文献：
  名称：

  Cahn; Penfold; Simonsen, Journal of the Chemical Society, 1931, p. 3140

  摘要：

  DOI：

文献信息

• Novel Tdp1 Inhibitors Based on Adamantane Connected with Monoterpene Moieties via Heterocyclic Fragments
  作者：Aldar A. Munkuev、Evgenii S. Mozhaitsev、Arina A. Chepanova、Evgeniy V. Suslov、Dina V. Korchagina、Olga D. Zakharova、Ekaterina S. Ilina、Nadezhda S. Dyrkheeva、Alexandra L. Zakharenko、Jóhannes Reynisson、Konstantin P. Volcho、Nariman F. Salakhutdinov、Olga I. Lavrik

  DOI：10.3390/molecules26113128

  日期：——

  Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising target for anticancer therapy due to its ability to counter the effects topoisomerase 1 (Top1) poison, such as topotecan, thus, decreasing their efficacy. Compounds containing adamantane and monoterpenoid residues connected via 1,2,4-triazole or 1,3,4-thiadiazole linkers were synthesized and tested against Tdp1. All the derivatives exhibited inhibition at low micromolar or nanomolar concentrations with the most potent inhibitors having IC50 values in the 0.35–0.57 µM range. The cytotoxicity was determined in the HeLa, HCT-116 and SW837 cancer cell lines; moderate CC50 (µM) values were seen from the mid-teens to no effect at 100 µM. Furthermore, citral derivative 20c, α-pinene-derived compounds 20f, 20g and 25c, and the citronellic acid derivative 25b were found to have a sensitizing effect in conjunction with topotecan in the HeLa cervical cancer and colon adenocarcinoma HCT-116 cell lines. The ligands are predicted to bind in the catalytic pocket of Tdp1 and have favorable physicochemical properties for further development as a potential adjunct therapy with Top1 poisons.

  酪氨酸-DNA磷酸二酯酶1（Tdp1）是抗癌治疗的一个有前途的靶点，因为它能够对抗拓扑异构酶1（Top1）毒素的影响，如托泊替康（topotecan），从而降低它们的疗效。含有金刚烷和单萜类残基，通过1,2,4-三唑或1,3,4-噻二唑连接剂连接的化合物已经合成并对Tdp1进行了测试。所有衍生物在低微摄或纳摄浓度下表现出抑制作用，其中最有效的抑制剂的IC50值在0.35-0.57 µM范围内。细胞毒性在HeLa、HCT-116和SW837癌细胞系中进行了测定；中等CC50（µM）值从中十几到100 µM无效不等。此外，在HeLa宫颈癌和结肠腺癌HCT-116细胞系中，柠檬醛衍生物20c，α-蒎烯衍生物20f、20g和25c，以及柠檬醛酸衍生物25b被发现与托泊替康联用具有增敏作用。 预测这些配体将结合在Tdp1的催化口袋中，并具有有利的物理化学性质，可进一步作为与Top1毒素联合治疗的潜在辅助疗法进行开发。
• Polyhydroxyphenol derivatives and preventive and therapeutic agents for bone and cartilage diseases containing the same
  申请人：Hoechst Marion Roussel

  公开号：US06177474B1

  公开（公告）日：2001-01-23

  Compounds useful as preventive and therapeutic agents for bone and cartilage diseases; and drug compositions containing the same. The compounds are polyhydroxyphenol derivatives of general formula (I) and quinione analogues derived therefrom (wherein R1 is alkyl, optionally substituted benzyl or optionally substituted aryl; R2 is hydrogen, alkyl, alkenyl or optionally substituted benzyl; R3 is hydrogen, alkyl, alkenyl, optionally substituted benzyl, hydroxyl, alkoxy, alkenyloxy or optionally substituted benzyloxy; R4 is hydrogen, alkyl, alkenyl, optionally substituted benzyl or hydroxyl; and R5 and R6 are each independently hydrogen, alkyl, alkenyl or optionally substituted benzyl). The polyhydroxyphenol derivatives and the quinone analogues exhibit a potent inhibitory activity against bone resorption and are useful as preventive and therapeutic agents for bone and cartilage diseases.

  具有预防和治疗骨骼和软骨疾病作用的化合物；以及含有这些化合物的药物组合物。这些化合物是通式(I)的多羟基酚衍生物和由此衍生的醌类似物（其中R1是烷基、可选择取代的苄基或可选择取代的芳基；R2是氢、烷基、烯烃基或可选择取代的苄基；R3是氢、烷基、烯烃基、可选择取代的苄基、羟基、烷氧基、烯烯氧基或可选择取代的苄氧基；R4是氢、烷基、烯烃基、可选择取代的苄基或羟基；而R5和R6各自独立地是氢、烷基、烯烃基或可选择取代的苄基）。这些多羟基酚衍生物和醌类似物表现出强大的抑制骨吸收活性，并且可用作预防和治疗骨骼和软骨疾病的药物。
• Studies on the Constituents of Lespedeza homoloba NAKAI. I. The Structure of Lespedeol A
  作者：AKIRA UENO、MASAHIRO ICHIKAWA、TOSHIO MIYASE、SEIGO FUKUSHIMA、YASUHISA SAIKI、KUNIO MORINAGA

  DOI：10.1248/cpb.21.1734

  日期：——

  A new isoflavanone derivative named lespedeol A was isolated from the bark of Lespedeza homoloba NAKAI. The structure was presumed to be 2', 4', 5, 7-tetrahydroxy-6-geranylisoflavanone by spectral and chemical data, and this presumption was confirmed by the synthesis of 2', 4', 7-trimethoxy-5-hydroxy-6-tetrahydrogeranylisoflavone derived from lespedeol A.

  从胡枝子 (Lespedezahomoloba NAKAI) 的树皮中分离得到一种新的异黄烷酮衍生物，命名为胡枝子醇 A。通过光谱和化学数据推测该结构为2',4',5,7-四羟基-6-香叶基异黄烷酮，并通过2',4',7-三甲氧基-5-羟基-的合成证实了这一推测。 6-四氢香叶基异黄酮，源自胡枝子醇 A。
• Liquid crystal compounds with branched or cyclic end groups
  申请人：——

  公开号：US20040206933A1

  公开（公告）日：2004-10-21

  The use of a mesogenic compound having a terminal end chain comprising carbon, oxygen, or sulphur, which has at least one pendent C 1-4 alkyl, C 1-4 alkoxy or a cycloalkyl ring, arranged no more than 6 atoms from the end of the chain either decreasing the melting point, increasing the clearing point, increasing the speed of switching and/or increasing the tilt angle of a liquid crystal mixture. Examples of such compounds are of formula (I) where M is a mesogenic core group, and X and Y are terminal groups, provided that at least one group X or Y is a group of sub-formula (i) where Z 1 , Z 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , s, q, m and n are as defined in the specification. Novel compounds of formula (I) are also described and claimed. 1

  使用具有末端端基的向列相化合物，其包含碳、氧或硫，并且具有至少一个悬挂的C1-4烷基、C1-4烷氧基或环烷基，离链末端不超过6个原子，可以降低液晶混合物的熔点、提高清晰点、增加切换速度和/或增加倾斜角度。这些化合物的例子是公式(I)的化合物，其中M是向列相核心基团，X和Y是末端基团，但至少一个基团X或Y是子公式(i)的基团，其中Z1、Z2、R1、R2、R3、R4、R5、R6、R7、s、q、m和n如规范中所定义。还描述和声明了公式(I)的新化合物。
• Elaboration of the Effective Multi-Target Therapeutic Platform for the Treatment of Alzheimer’s Disease Based on Novel Monoterpene-Derived Hydroxamic Acids
  作者：Yulia Aleksandrova、Aldar Munkuev、Evgenii Mozhaitsev、Evgenii Suslov、Dmitry Tsypyshev、Kirill Chaprov、Roman Begunov、Konstantin Volcho、Nariman Salakhutdinov、Margarita Neganova

  DOI：10.3390/ijms24119743

  日期：——

  Novel monoterpene-based hydroxamic acids of two structural types were synthesized for the first time. The first type consisted of compounds with a hydroxamate group directly bound to acyclic, monocyclic and bicyclic monoterpene scaffolds. The second type included hydroxamic acids connected with the monoterpene moiety through aliphatic (hexa/heptamethylene) or aromatic linkers. An in vitro analysis

  首次合成了两种结构类型的新型单萜基异羟肟酸。第一类化合物由直接与无环、单环和双环单萜骨架结合的异羟肟酸酯基团组成。第二种类型包括通过脂肪族（六/七亚甲基）或芳香族接头与单萜部分连接的异羟肟酸。生物活性的体外分析表明，其中一些分子具有强大的 HDAC6 抑制活性，化合物结构中存在的连接区域起着关键作用。特别是，发现在 Cap 基团中含有六和七亚甲基接头和 (-)-perill 片段的异羟肟酸对 HDAC6 表现出优异的抑制活性，IC50 的亚微摩尔范围为 0.56 ± 0.01 µM 至 0.74 ± 0.02 µM。抗自由基活性的研究结果表明，某些异羟肟酸具有中等清除 2,2-二苯基-1-苦基肼 (DPPH) 和 2ROO• 自由基的能力。DPPH自由基清除活性与氧自由基吸收能力（ORAC）值的相关系数为R2=0.8400。此外，具有基于对位取代肉桂酸的芳族接头的化合物，具有单环对薄荷烯骨架作为